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description=3 posts published by milkshake during September 2025;

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september, 2025, org, prep, daily, 30, 28, 18, bis, iodomethyl, pyridine, tricyclic, aldol, product, of, hexanal, with, cyclohexanone, anhydrous, cecl3, 2licl, solution, in, thf,

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september 2025 org prep daily org prep daily september 30 2025 2 6 bis iodomethyl pyridine filed under procedures milkshake 9 18 am 2 6 bis chloromethyl pyridine 17 70 g 100 5 mmol tci and sodium iodide 45 0 g 300 mmol in a 0 5 l round flask was combined in anhydrous acetone 200 ml without cooling and the mixture was stirred in a closed flask for 12 hours 1 h nmr in d 6 acetone indicated complete conversion the precipitated nacl was removed by vacuum filtration and rinsed with additional acetone the combined filtrates were slowly evaporated on rotovap from ambient water bath to dryness the obtained solids were suspended in water 0 5 l vigorous stirring for 15 min to remove nai excess the precipitated product was collected by filtration on a sintered glass buchner funnel rinsed thoroughly with water 0 5 l dried by suction of air 2 hours and then in high vacuum the yield was 35 93 g 99 5 of theory of a cream colored heavy crystalline solid the material is an irritant and it is best stored in a freezer 1 h cdcl 3 600 mhz 7 554 t 7 2hz 1h 7 235 d 7 2hz 2h 4 460 s 4h 13 c cdcl 3 150 mhz 158 30 2c 138 07 121 88 2c 6 10 2c leave a comment september 28 2025 tricyclic aldol product of hexanal with cyclohexanone filed under procedures milkshake 6 36 am first n hexanal was redistilled at reduced pressure b p 40 50 o c at 0 1 bar there was a substantial amount of oligomers left in the distillation residue from an old bottle in a 0 5 round 2 neck flask with an air cooled reflux condenser and a pressure equalized addition funnel flushed with ar cyclohexanone 200 ml used without purification was combined with a solution of koh 1 4 g pellets 85 grade in anhydrous pure non denatured etoh 23 ml the mixture was heated on a 75 o c oil bath and a solution of freshly distilled hexanal 21 5 g 214 5 mmol in anh pure etoh 22 ml was added dropwise very slowly over a 4 h period with stirring at 75 o c after the complete addition the mixture was stirred at 75 o c for extra 16 hours the reaction mixture was then cooled on ice bath and stirred on ice overnight the next morning the melted ice bath was replaced with fresh ice and stirring was continued for extra 2 h the precipitated product was collected by filtration on a large glass buchner funnel rinsed with small portions of ice chilled ether 3 x 20 ml then thoroughly rinsed with ice cold water 200 ml and dried by air suction overnight the yield was 39 70 g of a white fluffy odorless solid 66 of theory pure by nmr and tlc additional 3 49 g of impure material was obtained from the filtrates but this wasn t really worth the workup effort and evaporating the excess of cyclohexanone in vacuo 13 c and dept cdcl 3 150 mhz 220 08 c o 78 45 c oh 59 91 ch 48 41 ch 45 07 ch 42 51 ch 36 74 ch 2 32 02 ch 2 29 31 ch 2 28 74 ch 2 28 70 ch 2 26 51 ch 2 26 26 ch 2 25 56 ch 2 22 67 ch 2 21 24 ch 2 20 41 ch 2 14 13 ch 3 1 h cdcl 3 600 mhz 2 425 br m 1h 2 167 br m 2h 2 033 br m 1h 1 954 m 1h 1 872 m 2h 1 768 m 6h 1 655 br s 1h 1 596 br m 2h 1 462 m 1h 1 347 br d 11 4hz 1h 1 266 br m 8h 1 094 m 1h 0 851 t 7 2hz 3h leave a comment september 18 2025 anhydrous cecl3 2licl solution in thf filed under procedures milkshake 1 43 pm anhydrous cecl3 2licl complex in anh thf can be conveniently prepared by combining beads of anh cecl3 supplied in ampoule aldrich with 2 1 2 5 eq of pre dried licl in anh thf and stirring overnight under ar but since anhydrous cecl3 is far more expensive than its heptahydrate form krasovskiy and knochel developed a procedure for preparing this anhydrous solution fom cecl3 7h2o and licl angew chem int ed 2006 45 497 500 doi 10 1002 anie 200502485 their drying procedure is somewhat finicky since the last traces of hydrate water are difficult to remove and hydrolysis of cecl3 hydrates to insoluble oxychlorides needs to be minimized the drying is performed in several stages with attention to stirring and dehydration temperature and their procedure includes filtration of anhydrous thf solution from crushed molecular sieves which is best performed within a glovebox what follows is a modified version of the procedure a 1l round flask with a large egg shaped stir bar it is preferable to use a flask with 29 42 joint so that a larger stir bar can be used was charged with 52 0 g of cecl3 7h2o 0 14 mol and 12 0 g of licl 0 283 mol without a solvent the loosely capped flask was placed on a 100 105 c oil bath and heated and gently stirred until the solids liquified in their own crystal water and all chunks dissolved with formation of a viscous solution this took about 1 hour high vacuum was then applied with an additional cold trap cooled by liquid nitrogen added in between the flask and the pump cold trap to condense the liberated water and the material was dried at 100 105c and 0 05 torr for 3 hours the material in the flask solidified into a porous white solid and stirring became impossible after 3 hours the flask was removed from the heating bath cooled under ar to ambient temperature using a long spatula the stirbar was liberated and the solids were crushed into chunks within the reaction flask the material drying was incomplete at this stage 4 g of water remaining the solids were further dry stirred on a 100 105 c bath at 0 05 torr for 7 hours and then cooled to room temp under ar 0 2 g of water remaining 30 ml of neat tms cl 0 236 mol was then added the flask was equipped with an efficient reflux condenser and the slurry was stirred at reflux on a 85 90 c bath under a blanket of nitrogen sweeping the top of the condenser for 10 hours the tmscl tms 2o in the flask was removed under vacuum and the solids were dried with dry stirring on a 100 105 c bath and 0 05 torr overnight 12 h the obtained heavy white powdered solids were combined with anh thf about 0 45 l under ar mildly exothermic and the slurry was vigorously stirred under ar for 4 hours until the solids mostly dissolved and no material remained stuck on the flask walls the resulting milky solution was allowed to settle for 3 hours without stirring and the clear solution was transferred via canula into a 0 5 l schlenk storage flask containing activated 3a molecular sieves 20 g pellets the solution volume was adjusted by anh thf addition to a 500 ml pre scored mark and allowed to settle overnight this produced 0 5 l of approx 0 28 m cecl3 2licl solution comments 1 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 2025 october 2025 september 2025 april 2019 march 2019 december 2018 june 2018 september 2017 august 2017 march 2016 october 2015 august 2015 july 2015 june 2015 march 2015 november 2014 july 2014 may 2014 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