1-Acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one → 1-Acetoxy-3-methoxyestra-1,3,5(10)-trien-17beta-ol

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Reaction Steps

A solution of 1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one (4.9 g, 14.3 mM) in 250 ml of ethanol is shaken with PtO2 (1 g) under N2 at 40 psi for 7 hrs. After filtration and evaporation of the solvent in vacuo, the oily residue is chromatographed on 250 g of neutral silica gel, initially eluting with benzene and finally progressing to 5% ethyl acetate:benzene. Evaporation of the solvent in vacuo, followed by recrystallization from ether:hexane gives 1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17β-ol, yield 2.35 g (48%), m.p. 107°-110° C.

Provenance & Evidence