Water → HCID 12796509, compound

Participants

Reaction Steps

Sodium hydride (0.330 g) was carefully added to sodium dried tetrahydrofuran (10 ml) under nitrogen. Methyl triphenylphosphonium bromide (4.9 g) was added as a suspension in dry tetrahydrofuran (30 ml) followed by 3α-acetoxy-5α-androstane-11,17-dione (1.2 g) also in dry tetrahydrofuran (20 ml). The reaction mixture was refluxed for 3/4 hr. then cooled and poured into water. The product was extracted into ethyl acetate and the organic solution was washed with water, dried (Na2SO4) and evaporated. The residual oil was triturated with ether, the insoluble material was removed by filtration and the solid obtained by evaporation of the mother liquor was purified by chromatography over silica(ethyl acetate:petroleum ether 1:1) and recrystallisation from ether/petrol to give the title compound (0.695 g), m.p. 140°-1°, [α]D +44°.

Provenance & Evidence