Diethylamine → HCID 14217110, compound

Participants

Reaction Steps

A solution consisting of 27.6 g (0.098 mol) of mesylate 9, 20.5 ml of diethylamine and 250 ml of methylene chloride was heated at reflux temperature for 2 hrs under an atmosphere of argon. The resultant solution was cooled, concentrated in vacuo and the residue filtered through a column of silica gel (125 g) using ethyl acetate as the eluent. The fractions containing product (as determined by thin layer chromatography) were combined and concentrated in vacuo. Crystallization of the residue from ether/petroleum ether (bp 35°-60°) yielded Z-2-acetamido-4-methoxy-2-butenoic acid methyl ester (4) identical to the material obtained by the previous method (Examples 1 and 2). The mother liquors from the crystallization of 4 were concentrated in vacuo to yield an oil which contained a 1:1 mixture of 4 and E-2-acetamido-4-methoxy-2-butenoic acid methyl ester (5).

Provenance & Evidence