Sodium hydride → HCID 12796461, compound

Participants

Reaction Steps

Triphenylmethyl phosphonium bromide (7.5 g) was added to a suspension of sodium hydride (500 mg) in dry tetrahydrofuran (100 ml). The mixture was stirred at room temperature for 1.5 hours and then treated with 2β-ethoxy-3α-hydroxy-5α-androstane-11,17-dione (2.43 g). The mixture was refluxed for 1.5 hours, cooled and partitioned between ethyl acetate and water. The organic phase was washed with water, dried (Na2SO4) and evaporated in vacuo. Purification of the residue by chromatography over silica in ethyl acetate-petroleum ether (1:2) and crystallization from ether-petroleum ether afforded the titled compound (850 mg), m.p. 103°-108°, [α]D +25.5°.

Provenance & Evidence