Triphenylphosphine → HCID 54031575, compound

Participants

Reaction Steps

Diisopropyl azodicarboxylate (3.3 ml) was added to a solution of 4.5 g of triphenylphosphine in 90 ml of tetrahydrofuran at 0 ° C. and the mixture was stirred for 30'. To this mixture a solution of 2.1 g of 3α-hydroxy-androst-4-en-17-one (D'Incan E., Tetrahedron, 1982, 38, 1755) and 2.1 ml of thiolacetic acid in 90 ml of tetrahydrofuran was added dropwise and the residue was stirred for 1 hr at room temperature. The solvent was evaporated to dryness under reduced pressure and the crude product was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 95/5 as eluant to give 1.4 g of the title compound (IV-a) as a white solid.

Provenance & Evidence