Water → (17beta)-3-Oxoandrost-4-ene-17-carboxylic acid

Participants

Reaction Steps

To a stirred solution of 10.123 g. of potassium hydroxide in a mixture of 11.3 ml. of water and 180 ml. of methanol, is added 15 g. of the methyl carboxylate ester product of Step C. above, which is rinsed in with 22.5 ml. of additional methanol. The reaction mixture is placed in an oil bath and heated to reflux, where it is maintained overnight under a nitrogen atmosphere. The reaction mixture is then removed from the heat, concentrated briefly under the nitrogen stream, and then poured into a mixture of 750 ml. of ethyl acetate and 750 ml. of ice water containing 75 ml. of 2.5 N hydrochloric acid. The reaction mixture is shaken well and the resulting layers are separated. The aqueous layer is extracted again with 750 ml. of ethyl acetate and the combined ethyl acetate extracts are washed with 400 ml. of a saturated sodium chloride solution. The combined extracts are dried, filtered, and concentrated. The product is recrystallized from ethyl acetate to yield 11.78 g., m.p. 255° C.

Provenance & Evidence