Sodium Hydroxide → HCID 69104800, compound

Participants

Reaction Steps

195 ml of diethylaluminum cyanide (1.0 M, in toluene) was added in drops at a temperature of −5° C. under argon to a solution of 24.5 g of 11-ketosteroid 2 in 330 ml of toluene, and it was stirred for 1.5 hours while cooling was continued. Then, the mixture was poured onto 470 ml of ice-cooled 1N sodium hydroxide solution, stirred for 1 hour, extracted several times with ethyl acetate, and the collected organic phases were washed with water and brine and dried with magnesium sulfate. The chromatography of the evaporation residue on silica gel (solvent mixture: cyclohexane/ethyl acetate=4/1) yielded 3 as a foam in a yield of a total of 12.0 g (37%).

Provenance & Evidence