反应详情

A solution of 3β-Acetoxy-17-(2-chlorobenzimidazol-1-yl)-16-formylandrosta-5,16-diene (22a), (0.15 g, 0.304 mmol) in dry toluene (3 mL) was refluxed in the presence of chlorotris (triphenylphosphine) rhodium (I) (0.29 g, 0.311 mmol) for 60 h. After cooling to room temperature, the catalyst was removed by filtration through a Celite pad. The filtrate was evaporated, and the residue was purified by FCC [petroleum ether/EtOAc (8:2)] to give 0.04 g (28%) of pure 22b: mp 161-165° C.; IR (Neat) 2926, 2853, 1629, 1403, 1462, 1369, 1233, 1035, 847 cm−1; 1H NMR (500 MHz, CDCl3) δ1.05 (d, 6H, 18 and 19-CH3), 2.04 (s, 3H, 3β-OCOCH3), 4.62 (m, 1H, 3α-H), 5.44 (m, 1H, 6-H), 6.06 (s, 1H, 16-H), 7.33 (m, 1H, aromatic-H), 7.52 (m, 1H, aromatic-H), and 7.68 (m, 2H, aromatic-H).

1. customthe catalyst was removed by filtration through a Celite pad
2. customThe filtrate was evaporated
3. customthe residue was purified by FCC [petroleum ether/EtOAc (8:2)]