Isopropanol-hcl-water → 17alpha-Allyl-17-hydroxy-13-propylgon-4-en-3-one

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Reaction Steps

Treat dl-3-methoxy-13-propylgona-2,5(10)-dien-17-one (2.0 g) with allyl magnesium bromide to obtain a glass that is a mixture of dl-17α-allyl-3-methoxy-13-propylgona-2,5(10)-dien-17-ol (minor component) and the Δ5(10) -3-keto and Δ4 -3-keto compounds (major component). Hydrolyze the mixture (in two portions) with hydrochloric acid-isopropanol-water, then chromatograph and crystallize the resultant crude product to obtain the title compound (22% from the starting material), m.p. 135°-137°; ultraviolet absorption peak at 241.5 mμ (ε17,470), infrared maxima at 2.95 μ (OH), 6.03 μ, 6.18 μ (α,β-unsaturated carbonyl), 10.93 μ (R-CH=CH2).

Provenance & Evidence