Ethanol → HCID 86736929, compound

Participants

Reaction Steps

A solution of (Z)-2β-ethoxy-3α-hydroxy-5α-pregn-17(20)-en-11-one (710 mg) in refluxing ethanol (21 ml) was treated with a slurry of hydroxylammonium chloride (1.43 g) in 50% aqueous sodium hydroxide. After 24 hour refluxing, the cooled reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with water and evaporated to a froth (710 mg). This material was retreated with hydroxylamine as above to give a froth (800 mg) which was purified by preparative TLC (4% methanol in chloroform 22) and crystallisation from ethyl acetate/petrol to yield the title compound (220 mg), m.p. 176°-193°, [α]D +35.9°.

Provenance & Evidence