A Facile Reduction of Acid Anhydrides with Borane in the Presence of Lithium Chloride in Tetrahydrofuran

Carboxylic acid anhydrides are rapidly reduced with borane-lithium chloride (1:0.1) system to give corresponding alcohols (diols in the case of cyclic anhydride) quantitatively in tetrahydrofuran at room temperature. This reagent tolerates aromatic acid ester, nitro, and halide functional groups, however competitively reduces aliphatic ester and nitrile groups.