Chemistry of Sodium Borohydride and Diborane. IV. Reduction of Carboxylic Acids to Alcohols with Sodium Borohydride through Mixed Carbonic-Carboxylic Acid Anhydrides

摘要: Mixed carbonic-carboxylic acid anhydrides, prepared in situ from carboxylic acids and ethyl chloroformate, were reduced with sodium borohydride aqueous tetrahydrofuran to the corresponding alcohols fair yields. Under reaction condition examined, it was possible reduce carboxyl group selectively hydroxymethyl having functional groups such as nitro-, cyano-, amido-, ester-group, conjugated double bond. The general procedure for this is given.