Alumina-assisted reduction of carbonyl compounds with sodium borohydride in hexane

Abstract

A broad range of aliphatic, alicyclic, and aromatic ketones and aldehydes underwent smooth reduction with a combination of common, inexpensive laboratory reagents, sodium borohydride and chromatographic neutral alumina, in hexane to afford the corresponding alcohols in a selective and high-yielding manner under mild and neutral conditions. The NaBH4-based biphasic system can also successfully be used for the reduction of unsaturated substrates as well as steroidal and highly hindered ketones.