Methanol → 4-Methoxy-6-methylenandrost-4-ene-3,17-dione

Participants

Reaction Steps

To a stirred suspension of 4,5-epoxy-6-methylenandrostane-3,17-dione (0.630 g, 2 mmole) in methanol (63 ml) is added a 4N sodium hydroxide aqueous solution (6.3 ml). The resulting mixture is refluxed for 1 hr, cooled to room temperature, evaporated in vacuo, taken up with water, neutralised with a 37% hydrochloric acid solution and kept at 0°-5° C. overnight. The resulting precipitate is filtered off, washed with water, dried and purified by flash column chromatography on silica gel eluting with n-hexane: ethyl acetate 60:40. There are obtained 0.530 g (75% yield) of the title compound, m.p. 196°-198° C.

Provenance & Evidence