A Procedure for Diethoxymethylation of Ketones

Article abstract of DOI:10.1021/jo00325a023

Reaction of a number of ketones with diethoxycarbenium fluoroborate in the presence of N,N-diisopropylethylamine at low temperature in methylene chloride results in a preparatively useful conversion to α-(diethoxymethyl) ketones.The method is compatible with arene, nitrile, chloride, and ester functional groups.With unsymmetrically substituted ketones, it is regioselective for the less substituted α-position.In favorable cases α,α'-dialkylation occurs.Conjugated ketones react normally at the saturated position adjacent to the carbonyl group.The mechanism of the reaction is considered.