Defluorinative silylation toward a selective preparation of alpha-trimethylsilyl-alpha,alpha-difluoroacetates from trifluoroacetates

Electrochemical reduction of n-hexyl trifluoroacetate la in MeCN, involving Bu4NBr, TMSCl, and Et3N using an H-type divided cell equipped with carbon plate as an anode and lead plate as a cathode at 50 degrees C, provided n-h exyl alpha-trimethylsilyl-alpha,alpha-difluoroacetate 2a in 62% yield, whic h is a promising precursor of an alkoxycarbonyldifluoromethyl carbanion equ ivalent and can be alkylated at the alpha-carbon by fluoride ion catalysis.