Hydrochloric Acid → Androsta-1,4-diene-3,17-dione, 4-chloro-6-methylene-

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Reaction Steps

A solution of 4,5-epoxy-6-methylenandrost-1-ene-3,17-dione (1.0 g) in glacial acetic acid (10 ml) was treated with gaseous hydrogen chloride for 30 min at room temperature The precipitate was filtered off, washed with diethyl ether, dried and chromatographed on silica gel using hexane/ethyl acetate to yield 0.8 g of pure 4-chloro-6-methylenandrosta-1,4-diene-3,17-dione. Found: C 72.40, H 6.91, Cl 10.53; C20H23ClO2 requires: C 72.61, H 7.01, Cl 10.72. N.M.R. δp.p.m.: 0.84 (3H, s); 1.24 (3H, s); 5.13 (1H, s); 5.43 (1H, s); 6.37 (1H, d); 7.08 (1H, d). MS (m/z): 330.

Provenance & Evidence