p-Toluenesulfonic acid → HCID 53969888, compound

Participants

Reaction Steps

A solution of 6β-acetoxycholestan-3-one (1) (1215 mg, 2.74 mmol) of isopropenyl acetate (15 ml) was refluxed in the presence of ρ-toluenesulfonic acid (20 mg) under argon for 3 hr. Most of the solvent was removed and the concentrated mixture was extracted with ethyl acetate. The extract was washed with saturated NaHCO3, and brine, and dried over MgSO4. The residue obtained upon evaporation of the solvent was purified by column chromatography on silica gel (40 g). Elution with benzene gave the enol-acetate (2) (1265 mg, 95%), glass; δ0.71(3H, s, 18-H3), 0.88(6H, d, J=6 Hz, 26- and 27-H3), 0.91(3H, d, J=6 Hz, 21-H3), 1.02(3H, s, 19-H3) 1.08 and 1.11 (6H, Sx2, 2- and 6-acetyl), 5.03(1H, m, 6α-H), and 5.23(1H, dd, J=5 and 2 Hz).

Provenance & Evidence