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description=6 posts published by milkshake during May 2007;

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may, 2007, on, org, prep, daily, 31, 26, 21, 18, 16, my, chemical, kinks, and, fetishes, tpap, oxidation, alloc, piperidinecarboxaldehyde, septum, bottles, mitsunobu, aryl, ether, formation, piperidinol, with, hydroxypyridine, using, glass, tlc, plates, chlorofuroic, acid,

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(5), bottles (5), don (5), love (5), smell (5), february (4), 2012 (4), 2013 (4), 2025 (4), chemistry (4), after (4), reaction (4), dissolved (4), ethyl (4), acetate (4), organic (4), highvac (4), shiny (4), marble (4), quite (4), cutter (4), plate (4), store (4), common (4), hard (4), used (4), does (4), cutting (4), plates (4), side (4), pph3 (4), thf (4), period (4), hour (4), etoac (4), whenever (4), dry (4), chemical (4), cap (4), bottle (4), because (4), problem (4), solutions (4), watch (4), tpap (4), pure (4), make (4), log (3), wordpress (3), com (3), other (3), 2006 (3), 2014 (3), more (3), sensitive (3), chlorine (3), acid (3), clean (3), 400mhz (3), diluted (3), dissolution (3), product (3), aldrich (3), obtained (3), crystalline (3), white (3), couple (3), find (3), should (3), tlcs (3), expensive (3), tip (3), where (3), strips (3), nice (3), their (3), ones (3), screw (3), piperidinol (3), cooled (3), filtrates (3), cyclohexane (3), hexane (3), stuff (3), put (3), seal 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alcohol (2), dead (2), 0hz (2), 8hz (2), hydroxypyridine (2), until (2), dropwise (2), cooling (2), hours (2), small (2), h2o2 (2), few (2), filtered (2), pad (2), 20ml (2), crystallize (2), column (2), close (2), total (2), needles (2), pressure (2), resistant (2), square (2), pierced (2), thumb (2), air (2), fresh (2), well (2), bht (2), before (2), hydrocarbon (2), grignards (2), buli (2), moisture (2), same (2), goes (2), fridge (2), changes (2), afterwards (2), hood (2), what (2), distance (2), sureseal (2), keep (2), florida (2), catalyst (2), less (2), 85g (2), piperidinemethanol (2), anh (2), reach (2), ambient (2), purified (2), odor (2), spectra (2), methanol (2), 160ml (2), resulting (2), pale (2), 2hz (2), pleasing (2), bulb (2), kind (2), boiling (2), thing (2), its (2), morning (2), hydrogen (2), balloons (2), brownish (2), vapours (2), nitrogen (2), cleaning (2), mix (2), tiny (2), bits (2), smoke (2), liquid (2), sink (2), mysterious (2), own (2), pet (2), turn (2), lamp (2), strongly (2), refractive (2), just (2), crystals (2), crystal (2), kids (2), furfural (2), collapse, bar, manage, subscriptions, view, reader, content, privacy, already, join, 179, subscribers, blog, meta, xfn, valid, xhtml, create, archives, 2016, 2026, search, categories, questions, mechanisms, lit, highlights, destruction, krest17, industry, life, chris, douglas, behold, idle, words, edible, serious, eats, stellen, fuer, chemiker, practical, fragments, portal, flask, med, chemist, pipeline, chemjobber, pages, resources, bug, older, posts, substrates, often, oxidized, presence, scavenger, isobutylene, etc, chlorite, phenolic, arylacetone, substrate, soc, perkin, 1980, 136, 140, 376, 291, 702, 13c, 100mhz, 158, 144, 139, 120, 109, 147, chlorofurfural, 823, 305, 150ml, 50g, naclo2, 58g, tech, 14mmol, hplc, indicated, within, golden, containing, cl2, clo2, twice, 2x100ml, 100ml, sulfate, 30ml, gentle, heating, dryness, 893, chlorofuroic, stole, construction, boston, carried, 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necessary, keeping, bottled, compounds, healthy, dislike, acros, integrity, top, cannot, trusted, had, fairly, experience, fluka, humid, southern, without, review, synthesis, 1994, 639, 666, typical, loading, oxidations, mol, large, scale, experiment, stopped, sideproducts, started, appearing, baseline, 56mmol, previous, step, methylmorpholine, oxide, 203mmol, activated, powdered, sieves, 38g, suspended, dichloromethane, 210ml, mecn, 40ml, slurry, 306mg, 87mmol, 1mol, vigorously, continued, additional, overnight, 250ml, 100g, remove, methyl, morpholine, crude, 250g, 18g, colorless, faint, mowed, grass, overall, 198, nmr, awfull, hydrate, parent, piperidine, k2co3, 130mmol, solids, phasic, neat, allyl, chloroformate, 0ml, 103, vigorous, 2x200ml, sat, nahco3, 200ml, mgso4, torr, 60c, protected, intermediate, 920, 280, 7hz, 174, 5hz, 503, 477, 3hz, 985, 239, 752, 643, 532, 994, piperidinecarboxaldehyde, glassware, flasks, totally, aesthetically, coffee, kugelrohr, explain, charms, pump, 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ery much if i were a huffer i d huff it in the morning acetone is nice too but it does not give much of a buzz i love the smell of pure ethanol this being a rather common condition but i also find the smell of methanol pleasantly mild and refreshing while isopropanol has the robust kick heptane is very nice it s just like pears to me and i do love the smell of furfural kids if you ever get into the rye snapps thing then furfural is the pure essence of it and also linalyl acetate total earl gray crystals pearl shiny flakes long needles and strongly refractive rhombs turn me on inoculation of supersaturated solutions and oils that makes the crystals grow like in some kind of accelerated movie one can melt pure sodium thiosulphate pentahydrate on a hot water bath it dissolves in its own crystal water and let it supercool by leaving it covered at room temp then add a tiny crystal and watch the action with proper side illumination this never fails to impress kids and adults alike phenyl salicylate is supposedly even prettier but it is a less common chemical in organic labs mysterious looking liquids especially pale yellow ones strongly refractive or with a bluish hint of fluoresence silvery blobs of molten na or k floating up and down in boiling solvents just like a lava lamp but shiny any chemical that is blue colored blue is the color of solvated electrons in birch reduction as you keep adding chunks of na or li into the inky blue the mix becomes suddenly copper bronze shiny liquid dry ice and liquid nitrogen whenever i carry an open bucket of dry ice pellets i love to blow and breathe into it the billowing fog is very soothing few bits of dry ice in the rotovap bath or lab sink fill it with a mysterious smoke if you have a soapy solution you can make bubbles float above the sink ontop of the co2 laden fog i love to dip my finger into n2 l briefly and feel the bubbly tingle as it boils around it but no cold if you don t overdo it the dance of nirogen dropplets and the fog you can make your own icecream or freeze a rubber hose then crush it with a mallet invaluable when feeling lonely or a kitten after you lyophilyzed your frozen pet you should soak it carefully with a thick mineral oil or silicone this will make your pet transluscent you can then turn it into a tastefull bed side lamp hydrogen balloons whenever we are about to have a close hurricane hit here in florida i like to do weather balloons i inflate a huge black trash bag with hydrogen and then watch it disappearing into distance over the menacing overcast windy skies luminously burning metals magnesium lithium aluminum with oxidizer quite harmful to look at with unprotected eyes as there is a major uv component in this white light bromine there is something very unsettling about the red brownish heavy vapours creeping in the hood liquified chlorine and bright yellow chlorine solution in ccl4 is more pleasing violet vapours of iodine best produced from nitrogen triiodide can make some stunning effects but cleaning the resulting brownish mess is not fun afterwards piranha solution when cleaning guey fritted buchner funnels with h2so4 h2o2 i love to feed the mix with tiny bits of paper and watch them disappear instantly in a puff of smoke clean glassware the chemglass flasks are totally pleasing aesthetically coffee can kugelrohr it is hard to explain the charms but bulb to bulb with a good pump rocks you would not believe what kind of hygroscopic high boiling polyamino hydroxy puddings one can purify on that thing the d6 dmso signal the old friend in its symmetrical quintupletifulness at two point five re assures me about the good health of other signals in the spectra the color of a fresh tetrakis in the morning the lemony yellow is the color of victory comments 18 may 26 2007 tpap oxidation 1 alloc 4 piperidinecarboxaldehyde filed under procedures milkshake 11 20 pm piperidine 4 methanol 10 0g 86 8 mmol was dissolved in mixture of thf 160ml and water 160ml and k2co3 18 0g 130mmol was added the mixture was stirred until complete dissolution of the solids 10 min the resulting bi phasic mixture was cooled to 0c after 20 min at 0c neat allyl chloroformate 11 0ml 103 5 mmol 1 2 eq was added dropwise with vigorous stirring over a 5 min period the mixture was stirred on ice bath for 1 hour then the bath was allowed to melt and reach ambient temperature over 3 hour period the reaction mixture was extracted with ether 2x200ml the organic extracts were washed with sat aqueous nahco3 200ml combined dried with mgso4 and evaporated the residue was dried on highvac 0 5 torr 60c y 16 85g 97 5 of the alloc protected piperidinemethanol intermediate as a pale yellow oil 1h d6 dmso 400mhz 5 920 m 1h 5 280 dq d 17 2hz q 1 7hz 1h 5 174 dq d 10 5hz q 1 6hz 1h 4 503 dt d 5 2hz t 1 6hz 2h 4 477 t 5 3hz 1h 3 985 br m 2h 3 239 t 5 8hz 2h 2 752 very br s 1h 1 643 m 2h 1 532 m 1h 0 994 m 2h 16 85g 84 56mmol of 1 alloc 4 piperidinemethanol from the previous step was combined with anhydrous n methylmorpholine n oxide 23 8g 203mmol 2 4 eq and activated powdered 4a sieves 38g the mixture was suspended in anh dichloromethane 210ml with added anh mecn 40ml 40 min stirring the slurry was cooled to 0c tpap 306mg 0 87mmol 1mol solid was added in one portion and the mixture was vigorously stirred at 0 5 c for 90 min under ar the cooling bath was allowed to melt and reach the ambient temperature over 2 hour period the stirring was then continued at rt for additional 9 hours overnight the reaction mixture was diluted with etoac 250ml filtered through a pad of silica 100g the silica was washed with etoac 0 5l the combined filtrates were evaporated and the residue dried on highvac to remove n methyl morpholine the obtained crude aldehyde 14 0g was purified on a column of silica 250g in hexane etoac 1 1 mixture 3l y 9 18g of a pure aldehyde as a colorless oil with a faint mowed grass odor 55 th 53 5 overall y lc ms esi 198 m 1 the 1h nmr spectra of the purified product was quite awfull because the product was a mixture of aldehyde hydrate with the parent aldehyde tpap review synthesis 1994 639 666 the typical catalyst loading in tpap oxidations is 5 mol in this large scale experiment i used less catalyst and stopped the reaction before complete conversion of the alcohol because some sideproducts started appearing on the baseline comments 10 may 21 2007 on septum bottles filed under procedures milkshake 9 49 pm i dislike septum bottles of anhydrous solvents from acros i found that the integrity of their screw top cap with wide septa cannot be trusted i have had a fairly good experience with aldrich fluka i keep a number of sensitive reagents and anhydrous solvents in sureseal bottles in humid southern florida without much problem couple of comments on keeping the sureseal bottled compounds healthy 1 it helps to pierce the septa only with thin needles gauge 19 20 whenever possible always put the sure seal bottles under positive pressure of dry ar when drawing stuff from them 2 i use a transparent polyethylene chemical resistant tape to re seal the septa crown cap i cut a 1 1 in square of the tape and affix it over the crown to cover the septa that was pierced and i compress the tape with a thumb to squeeze out air channels i replace the tape square with a fresh one whenever i use the bottle then i put the red plastic screw cap on the taped crown and parafilm it around with double folded parafilm strip the parafilm is doubled for better mechanical durability it is stretch wrapped and thumb compressed to seal up tightly the parafilming around the bottle red cap is not overly important but the taping the pierced septa is crucial a suitable solvent resistant polyethylene tape is available from vwr cat 11211 934 3 avoid commercial unstabilized anhydrous ether solvents because they don t store well buy the stabilized ones in medicinal chemistry a trace of bht is much lesser problem than peroxides if one does a very sensitive chemistry where bht interferes he should not be buying anhydrous solvents anyway but distill his ether solvents from a benzophenone ketyl still 4 don t buy lda or lihmds because these reagents are made very easily freshly before use and the quality of their commercial solutions is quite atrocious strong bases in thf do not store well buy hydrocarbon solutions of nahmds and khmds grignards in thf are usually fine 5 buli and sec buli solutions in hydrocarbon are stable at rt the air and moisture is the problem the same goes for many commercial grignard reagents don t put stuff in fridge that does not have to be refrigerated temperature changes cause pressure changes in the bottle and moisture condensation problem also grignards tend to crystallize in the fridge and are hard to re dissolve afterwards a cabinet under hood is where i store most of my organometallics 6 i don t like to share my septum bottles the same goes for the needless and syringes if there is no other alternative i hand over my septa bottle allways together with the polyethylene tape and with explicit reminders about what to do then quietly watch from distance and yell if necessary org prep daily stats are getting close to 100k total thanks for reading this stuff comments 37 may 18 2007 mitsunobu aryl ether formation 4 piperidinol with 2 hydroxypyridine filed under procedures milkshake 5 32 am 5 fluoro 2 hydroxypyridine 1 844g 16 3 mmol mixture with n boc 4 piperidinol 5 032g 25 mmol and pph3 6 82g in anhydrous thf 60ml was stirred under ar until complete dissolution 20 min the solution was cooled to 0c on ice bath and dead 40 solution in toluene 10ml aldrich 26 mmol was added dropwise over a 20 min period the ice cooling bath was allowed to expire over 90 min and the mixture was stirred at rt for 36 hours over weekend the unreacted pph3 was destroyed by addition of a small amount of concentrated h2o2 50 solution 0 5ml followed by few spoons of silica the mixture was stirred for 10 min then filtered through a pad of silica 2x2in the silica was washed with ethyl acetate 400ml the combined filtrates were evaporated and the residue was dried on highvac the residue was diluted with toluene 20ml and cyclohexane 20ml was added the mixture was allowed to crystallize for 1 hour the precipitate pph3 o was removed by filtration and washed with some 2 1 cyclohexane toluene mixture the filtrates were evaporated the residue was dissolved in a small volume of cyclohexane toluene 1 1 mixture applied onto a column of silica 80g in hexane and eluted with ethyl acetate linear gradient 0 to 20 etoac in hexane combiflash lc station with uv detection y 4 526g 93 5 of a white crystalline solid 1h d6 dmso 400mhz 8 126 d 3 0hz 1h 7 673 td t 8 4hz 3 1hz 1h 6 848 dd 9 0hz 3 6hz 1h 5 083 m 1h 3 688 dt d 13 8hz t 4 6hz 2h 3 145 br m 2h 1 928 m 2h 1 522 m 2h 1 401 s 9h in this case the used phenol was much more expensive then the alcohol so the piperidinol and dead pph3 was used in excess comments 38 may 16 2007 on using glass tlc plates filed under procedures milkshake 2 07 pm we buy merck silica tlc glass plates 250um with uv indicator 20 20 cm we get them from emd through vwr for about 90 per pack of 25 after discount i divide each plate into 3 strips of equal size about 6 5 x20cm and i cut the strips into individual tlcs as i momentarily need them the width being determined by the number of reactions fractions standards that i need to run on the tlc side by side some people hate cutting their glass backed tlcs and buy pre cut ones expensive and one size only or use aluminum backed plates incompatible with several good tlc stains i found that cutting the glass plates is not hard to do and that crappy worn or damaged diamond cutter is the most common reason for frustrating results for example chemglass sells acceptable diamond cutters for reasonable price one has to clean the grease off the tip with some organic solvent and fix the wiggly headpiece with diamond tip onto the handle by loosening the screw rotating the handle and re fastening it silicon carbide disc pizza cutters can be also pretty good i have been sceptical about them but now i use a plate cutting contraption that has si c disc in it and it works fine one common beginners mistake is to double cut or push hard on the cutter if the used diamond cutter is sharp a hair thin nearly invisible cut made with one light slide works lot better than wide a trench dug in the glass through a screeching effort also it is important to use some straight solid ruler that does not bend sideways for cutting breaking the plate a nice plastic one has a y shaped profile and marks with different scales if you find yourself next to home depot you should buy a polished marble tile for your tlcs it is not expensive something like 5 a piece it serves as a perfectly flat surface with a sharp edge also the marble but not granite is quite soft so your cutter slips off the glass plate the impact on the tile will not damage the diamond tip the tile is also a good place where to store couple of pre cut tlc glass strips facing down but the tile has to be a real marble not a glazed ceramic i stole my marble tile at a construction site in boston and i carried it with me ever since through couple of jobs to san francisco and then back east again comments 30 5 chlorofuroic acid filed under procedures milkshake 4 37 am a solution of 5 chlorofurfural 823 mg 6 305 mmol in acetonitrile 25 ml was diluted with water 150ml and sulfamic acid 1 50g 15 4 mmol was added after complete dissolution naclo2 1 58g 80 tech product aldrich 14mmol solid was added in one portion and the mixture was stirred for 30 min at rt hplc indicated complete a conversion within 10 min the obtained golden yellow reaction mixture containing some dissolved cl2 and clo2 was extracted twice with ethyl acetate 2x100ml the organic extracts were washed with water 100ml combined dried with magnesium sulfate and evaporated the obtained crystalline residue was dissolved in acetonitrile 30ml with gentle heating and re evaporated to dryness dried on highvac y 893 mg 96 5 of a pearl shiny white crystalline solid 1h d6 dmso 400mhz 13 376 br s 1h 7 291 d 3 6hz 1h 6 702 d 3 6hz 1h 13c d dmso 100mhz 158 26 144 59 139 10 120 00 109 63 lc ms esi 145 147 m 1 more sensitive substrates are often oxidized in presence of chlorine scavenger isobutylene etc the chlorite sulfamic acid in aqueous acetone allowed clean oxidation with unprotected phenolic aldehyde arylacetone substrate j chem soc perkin 1 1980 136 140 comments 11 older posts pages about milkshake about org prep daily bug report chemistry resources chemistry chemjobber in the pipeline med chemist open flask org chem portal practical fragments stellen fuer chemiker edible links serious eats links to behold idle words categories chris douglas industry life krest17 lab destruction lit highlights mechanisms procedures questions uncategorized search archives january 2026 december 2025 november 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