Hydrogen Peroxide → 3-Methoxy-1,3,5(10),15-estratetraen-17alpha-ol

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1.9 g. of diphenyldiselenide is dissolved in 100 ml. of absolute ethanol and combined at room temperature with 500 mg. of sodium borohydride. After decolorization of the yellow solution, 2.5 g. of 16α,17α-epoxy-3-methoxy-1,3,5(10)-estratriene [B. Schoenecker et al., Z.Chem [Chemical News] 10 (6), (1910)] is added thereto, and the mixture is heated for 27 hours under reflux. After cooling to 0° C., 6 ml. of 30% H2O2 is added dropwise thereto, and the solution is gradually warmed to 50° C. After 2 hours, the solution is poured into ice water. The thus-precipitated product is vacuum-filtered, washed with water, taken up in methylene chloride, and dried over sodium sulfate. After the crude product has been chromatographed on silica gel with 5 - 7.5% acetone/hexane, 1.1 g. of 3-methoxy-1,3,5(10),15-estratetraen-17α-ol is isolated as an oily product.

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