反应详情

A solution of butyllithium (1.6 M, 3.44 mL, 5.5 mmol) was added at −20° C. to a solution of 1-methyl-3-phenyl-1H-indole (1b) (1.08 g, 5.3 mmol) in anhydrous tetrahydrofuran (20 mL) under a nitrogen atmosphere. After 1 hour, a solution of ethyl glyoxylate in toluene (50%, 1.1 mL, 5.5 mmol) was added. The reaction mixture was slowly warmed to room temperature for 2 hours, quenched with water (5 mL) and concentrated in vacuo. The residue was partitioned between dichloromethane (40 mL) and water (15 mL). The organic layer was washed with water (2×15 mL), brine (15 mL), dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired alcohol (1c) as a white solid (360 mg, 1.16 mmol, 22%).

1. customquenched with water (5 mL)
2. concentrationconcentrated in vacuo
3. customThe residue was partitioned between dichloromethane (40 mL) and water (15 mL)
4. washThe organic layer was washed with water (2×15 mL), brine (15 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customevaporated to dryness
8. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)