Diethyl Ether → 3-Acetoxy-17-(3-pyridyl)androsta-3,5,16-triene

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17-(3-pyridyl)androsta-4,16-dien-3-one (174 mg, 0.50 mmol) was dissolved in isopropenyl acetate (2 ml). p-Toluenesulfonic acid (130 mg, 0.68 mmol) was then added and the mixture heated at 80° C. for 12 h. After allowing to cool the mixture was poured into diethyl ether, washed with saturated aqueous sodium bicarbonate, dried (Na2CO3) and concentrated. Chromatography on elution with light petroleum--diethyl ether (1:1), afforded the title compound (86 mg, 44%), IR νmax 1755 cm-1, 1H-NMR (CDCl3) inter alia δ1.05 (6H,s,18-CH3 and 19-CH3), 2.15 (3H,s,COCH3) 5.44 (1 H,m,6-H), 5.72(1H,m,4-H), 6.00 (1H,m,16-H), 7.25 (1H,m,Py 5-H), 7.66 (1H,m,Py 4-H), 8.47 (1H,M,Py 6H), 8.63 (1H,m,Py 2-H). MS m/z 389 (M+).

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