Diiodomethane → (7alpha,14beta,15beta,17beta)-3-Methoxy-7-methyl-14,15-methyleneestra-1,3,5(10)-trien-17-ol

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Reaction Steps

i)—A solution of (7α,17β)-3-methoxy-7-methylestra-1,3,5(10),14-tetraen-17-ol [Segaloff, A. et al, Steroids 22, 99 (1973); 25.4 g] and diiodomethane (27 ml) in dry dichloromethane (500 ml) was cooled to 0° C. A solution of diethylzinc in hexane (15% wt., 300 ml) was added in 1 h and the reaction mixture was stirred for 21 h at room temperature. Ice was added and the mixture was poured into a saturated aqueous solution of ammonium chloride. The product was extracted into diethyl ether; the combined organic phases were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Column chromatography afforded (7α,14β,15β,17β)-3-methoxy-7-methyl-14,15-methyleneestra-1,3,5(10)-trien-17-ol (6.50 g).

Provenance & Evidence