Trimethyl phosphite → phosphoenol-3-chloropyruvate

Participants

Reaction Steps

To trimethyl phosphite (10 mmol) cooled at 0-10° C. was added dropwise ethyl dichloropyruvate (10 mmol). After addition, the ice-bath was removed and the reaction was allowed to proceed at 70° C. for one hour to give the ethyl/dimethyl ester of 3-chlorophosphoenolpyruvate. It was purified by flash chromatography (hexanes/ethyl acetate, 1:1, v/v) to give 1.5 g (58% yield) of 4:1 mixture of the Z- and E-isomers.

Provenance & Evidence