反应详情

温度

-10 °C

To a solution N-[2-(1-benzhydryl-5-chloro-1H-indol-2-yl)ethyl]-1-(3,4-dichlorophenyl)-methanesulfonamide (3.0 g, 5.14 mmol), triethylsilane (1.79 g, 15.4 mmol), and 4-(3-oxopropyl)benzoic acid ethyl ester (1.26 g, 6.16 mmol) in dichloromethane (30 mL) at −20 to −25° C. was added trifloroacetic acid (2.93 g, 25.7 mmol) during a period of 1 min. The mixture was warmed to −10° C. and stirred for 4 h. Saturated aqueous NaHCO3 (20 mL) was added. The mixture was extracted with EtOAc (150 mL). The organic extract was dried over Na2SO4. The solvent is evaporated. The residue is purified by column chromatography, using a mixture of heptane and EtOAc (4:1) as elute to give a white solid (2.25 g, 56%). 1H NMR (CDCl3): δ6.9-7.6 (m, Ph, CHPh2), 7.97 (d, 1H, J=1.6 Hz), 7.41 (d, 1H, J=1.9 Hz), 6.50 (d, 1H, J=8.9 Hz), 4.35 (dd, 2H, J=7.1, 14.3 Hz), 4.13 (m, 1H), 3.92 (s, 2H), 2.95 (m, 2H), 2.71 (m, 6H), 1.96 (m, 2H), 1.38 (t, 3H, J=7.1 Hz).

1. extractionThe mixture was extracted with EtOAc (150 mL)
2. extractionThe organic extract
3. dry with materialwas dried over Na2SO4
4. customThe solvent is evaporated
5. customThe residue is purified by column chromatography
6. additiona mixture of heptane and EtOAc (4:1)
7. washas elute