反应详情

To a cold (-78°) solution of indole (4.0 g, 34 mmol) in THF (120 mL) was added nBuLi (2.5M/Hexanes) over 5 minutes. The solution was warmed to -10° (ice/salt bath) for 15 minutes, re-cooled to -78° and TBDMS-Cl (5.8 g, 38 mmol) was added in THF (30 mL). The solution was held at 0° for 3 hours, cooled to -78° and N-Bromosuccinimide (6.0 g, 34 mmol) was added in one portion. The solution was stirred coldfor 2 hours and then was allowed to warm to ambient temperature at which time hexane/pyridine (100 mL) was added to the solution and the resulting suspension was filtered over Celite. The organics were evaporated and the residue quickly purified by flash chromatography (hexanes/methylene chloride 2:1) giving 8.5 g of the desired compound as a slightly purple solid.

1. temperatureThe solution was warmed to -10° (ice/salt bath) for 15 minutes
2. temperaturere-cooled to -78°
3. temperaturecooled to -78°
4. additionwas added to the solution
5. filtrationthe resulting suspension was filtered over Celite
6. customThe organics were evaporated
7. customthe residue quickly purified by flash chromatography (hexanes/methylene chloride 2:1)