SYNTHESIS OF α,β-EPOXY DIAZOMETHYL KETONES

Article abstract of DOI:10.1016/0040-4020(80)80105-0

The preparation of eighteen epoxy diazomethyl ketones 1 is described.Two general methods were developed.Firstly, treatment of the mixed anhydrides of glycidic acids and carbonic acid ester with diazomethane led to the title compounds in yields ranging from 17-74 percent.Secondly, glycidyl chlorides which were obtained from sodium glycidates and oxalyl chloride, gave the desired products upon treatment with diazomethane ( yields 60-74 percent).The required α,β-epoxy carboxylic esters were prepared by Darzens condensation and epoxidation of α,β-unsaturated esters, but in some cases also by reaction of α-oxo carboxylic esters with diazomethane.