Acetate → 17beta-Acetoxy-7alpha-methyl-10-(1,2-propadienyl)estr-4-en-3-one

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Diene 10, prepared from alcohol 26 by the procedure of Example 4, is converted to its 17-acetate by the procedure of Example 11. The crude acetate (352 mg, 1 mMole) in ether (2 ml) is added to an ethereal solution of lithium dimethylcopper prepared from 300 mg (2 mMole) of cuprous iodide and 2 ml (4 mMole) of a 2 M solution of methyl lithium in ether (5 ml) at -30° C. After 1 hour, the solution is allowed to warm to 0° C., then poured into water and extracted with ether. The combined ethereal extracts are washed with brine, then dried and evaporated. Recrystallization from ethyl acetate/hexane yields the product 27.

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