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description=2 posts published by milkshake during November 2010;

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november, 2010, org, prep, daily, 20, acetyl, ethoxyacrylic, acid, ethyl, ester, beta, ketoester, cyclization, with, aminotriazoles,

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november 2010 org prep daily org prep daily november 20 2010 2 acetyl 3 ethoxyacrylic acid ethyl ester e z filed under procedures milkshake 7 13 pm a mixture of ethyl acetoacetate 52 0g 399 mmol ethyl orthoformate 59 2g 399 mmol and acetic anhydride 81 6g 800 mmol in a 0 5l round flask was refluxed under nitrogen on a 150 c oil bath for 90 min the reflux condenser was replaced with a shortpath distillation apparatus and the formed ethyl acetate was distilled out from the reaction mixture at atmospheric pressure under nitrogen from a 150c oil bath this took additional one hour the cooled reaction mixture was then distilled at 6 torr from an oil bath 30 c to 90 c to remove the formed acetic acid the distillation residue was then fractionally distilled on highvac after a small fruity smelling front fraction few ml the desired product distilled at 75 82 c 0 25 torr the obtained main fraction of the product was re distilled on highvac b p 80 c 0 15 torr y 48 2g of a colorless slightly oily liquid the pure product has only a faint non fruity odor 1h nmr cdcl3 400mhz shows two sets of closely spaced signals of the e and z isomers approximately of equal height 7 671 s 0 5h 7 639 s 0 5h 4 251 m 4h 2 407 s 1 5h 2 346 s 1 5h 1 402 m 3h 1 339 m 6h note a condensation of this material 2 5 mmol with the diaminotriazole 2 0 mmol from the preceding experimental in acoh 5 ml at rt 10 min and then at 110 c for one hour followed by evaporation and precipitation of the residue with mecn provided the following cyclization product in 76 y 1h d6 dmso 400mhz 10 353 s 1h 9 010 s 1h 7 774 app d 8 8hz 2h 7 423 app d 8 8 hz 2h 4 370 q 7 1hz 2h 3 084 s 3h 2 976 s 6h 1 368 t 7 1hz 3h comments 16 november 4 2010 beta ketoester cyclization with aminotriazoles filed under procedures milkshake 11 02 am the diaminotriazole thf from the previous step 637mg 2 0 mmol was dissolved in acetic acid 5 ml cyclohexanone 2 carboxylic acid ethyl ester 0 48ml 3 mmol was added and the mixture was stirred at reflux on a 130c oil bath for 90 min the cooled reaction mixture was evaporated to dryness and the oily residue was suspended in acetonitrile 5ml with sonication the crystalline precipitate was collected by filtration washed with acetonitrile then dried by suction and on highvac y 664 5mg of a white crystalline solid 94 y 1h ddmso 400mhz 12 70 br s 1h 9 80 s 1h 7 69 dt d 8 6hz t 1 8hz 2h 7 38 dt d 8 8hz t 2 0hz 2h 2 97 s 6h 2 61 br t 5 7hz 2h 2 40 br t 5 9hz 2h 1 72 m 4h note using the same reaction conditions ethyl acetoacetate provided 92 y of a cyclization product cyclopentanone 2 carboxylic acid ethyl ester gave 55 5 y the product in this case crystallized directly from the reaction mixture and it was washed with acoh and then mecn the products were isomerically pure by 1h nmr and hplc comments 13 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 september 2013 july 2013 may 2013 april 2013 october 2012 september 2012 august 2012 january 2012 december 2011 november 2011 october 2011 july 2011 june 2011 april 2011 december 2010 november 2010 october 2010 september 2010 july 2010 june 2010 may 2010 march 2010 february 2010 january 2010 december 2009 november 2009 september 2009 august 2009 june 2009 may 2009 april 2009 march 2009 february 2009 november 2008 august 2008 july 2008 june 2008 march 2008 february 2008 january 2008 december 2007 november 2007 october 2007 september 2007 august 2007 july 2007 june 2007 may 2007 april 2007 march 2007 february 2007 january 2007 november 2006 october 2006 september 2006 meta create account log in rss comments rss valid xhtml xfn wordpress com blog at wordpress com subscribe subscribed org prep daily join 179 other subscribers sign me up already have a wordpress com account log in now privacy org prep daily subscribe subscribed sign up log in report this content view site in reader manage subscriptions collapse this bar loading comments write a comment email required name required website