Diisopropylamine → HCID 86738321, compound

Participants

Reaction Steps

A solution of lithium diisopropylamide, prepared from 0.26 ml of diisopropylamine and 0.85 ml of a 2.1 M solution of butyllithium and 5 ml of tetrahydrofuran is added to a solution of 640 mg of (chloromethyl)triphenylphosphonium chloride in 5 ml of tetrahydrofuran at -70° C. After 10 minutes at -70° C., a solution of 560 mg of 3,17-dioxo-5α-androstane-19-carboxaldehyde in 4 ml of tetrahydrofuran is added and the mixture is allowed to warm to room temperature. The mixture is then poured into water and extracted with ether. The solvent is evaporated and the residue is purified by flash chromatography on silica gel in 50% ethyl acetate-hexane to give 10-(3-chloroprop-2-enyl)-5α-estrane-3,17-dione as a mixture of isomers.

Provenance & Evidence