Water → (17beta)-13-Ethyl-3-methoxygona-1,3,5(10),15-tetraen-17-ol

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Reaction Steps

At 0° C. and under argon, 4 ml. of a 2-molar tert.-butyllithium solution in pentane is added to 450 mg. of 16α,17α-epoxy-3-methoxy-18-methyl-1,3,5(10)-estratriene in 12 ml. of ether. After 1 hour, the solution is diluted with ether, gently mixed with water, washed neutral, and dried over sodium sulfate. After purifying the crude product by preparative layer chromatography (system: hexane/ethyl acetate = 7 : 3), 140 mg. of 3-methoxy-18-methyl-1,3,5(10),15-estratetraen-17α-ol is obtained as an oily product. [α]D 20 = -105°.

Provenance & Evidence