Diisobutylaluminumhydride → HCID 53866782, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of the ethylene ketal of ethyl (4-keto-2-phenyl-cis-cyclohexyl)acetate (5.0 g.) in dry toluene (100 ml.), cooled at -70° C. under argon, was treated dropwise with a 1M solution of diisobutylaluminium hydride in toluene (18 ml.). The mixture was stirred at -70° C. for 35 minutes, quenched by addition of ethanol (5 ml.) and allowed to warm up to ambient temperature. Water (100 ml.) was then added and the subsequent mixture was extracted with ether (4×100 ml.). The combined extracts were washed successively with water (2×100 ml.) and brine (1×100 ml.), dried (MgSO4) and evaporated. The residue obtained was purified by flash chromatography on silica, eluting with ether/hexane (3:7 v/v), to give the ethylene ketal of (4-keto-2-phenyl-cis-cyclohexyl)acetaldehyde (3.92 g.) which was used immediately in the Wittig reaction.

Provenance & Evidence