Hydrochloric Acid → Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

Participants

Reaction Steps

Dissolve 13β-ethyl-3-methoxy-gona-2,5(10)-dien-17β-ol (0.47 g.) in hot methanol (25 cc.). Add 3N hydrochloric acid (15 cc.) and keep the mixture at 70° C. under nitrogen for 1 hour. Add water and work up with ether and chromatograph the resulting gum on activated alumina (40 g.). Elute with ether to give a fraction (0.2 g.) which on recrystallization from light petroleum gives 13β-ethyl-17β-hydroxy-gon-4-en-3-one; m.p. 153°-5° C; ultra-violet absorption peak at 240 mμ (ε 16,300).

Provenance & Evidence