Hydrochloric Acid → 15,15-Dimethylestra-1,3,5(10)-triene-3,17beta-diol

Participants

Reaction Conditions

Reaction Steps

Representative Procedure: Diisobutylaluminum hydride (0.5 ml; 1.5M; 0.75 mmol) was added to a solution of the 5,15-dimethyl-17β-alcohol (12) in dry toluene (5 ml). The solution was heated to refluxing temperature for 24 h. The mixture was cooled to 0° C., saturated aqueous ammonium chloride was added, and the aqueous phase was further acidified with dilute HCl. The standard work-up (ethyl acetate) gave 15,15-dimethylestra-1,3,5(10)-triene-3,17β-diol (16) (43 mg; 90%), m.p. 167-170 (from ethyl acetate); [α]D +49° (c 1.1 ethanol) (Found; C, 79.6; H, 9.3%; M+, 300. C20H28O2 requires C, 80.0; H, 9.4%; M, 300).

Provenance & Evidence