Ethyl Acetate → 5α-Cholest-8(14)-en-3β-ol

Participants

Reaction Steps

50 g of cholestadiene were dissolved in 800 ml of dry ethyl acetate to which 30 ml of acetic acid had previously been added and after addition of 1.5 g of platinum oxide the mixture was transferred to an autoclave of 2 1 volume. Hydrogenation was carried out at 50° C. and 10 atm hydrogen pressure and was complete after 24 h. After reaction was complete, the catalyst was filtered off, the solvent was concentrated in a rotary evaporator and the doristerol obtained was recrystallized from ethanol. Yield: 42.5 g (88.5%). The purity of the substance was confirmed with the aid of 1H-NMR and 13C-NMR spectroscopy. 17 g of 4-(propen-2-oxy)benzoyl chloride and 32 g of doristerol were dissolved in 200 ml of dry toluene and heated to reflux for 15 h. The solvent was then distilled off and the residue was recrystallized from ethanol; yield: 44.9 g (99%), m.p. 92° C. (n*105i).

Provenance & Evidence