反应详情

温度

0 °C

To a solution of 1H-indole-4-carbaldehyde (1) (1.0 g, 6.88 mmol) in dimethylformamide (DMF, 35 mL) was added potassium t-butoxide (KOtBu, 1.16 g, 10.32 mmol) at 0° C. After the resulting solution was stirred for 30 min at 0° C., 2-bromopentane (2) (1.05 ml, 8.27 mmol) was added dropwise, and the reaction solution was warmed up to room temperature gradually and stirred for 12 h at room temperature. Water (5 ml) was added to quench the reaction. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with H2O (40 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography (6:1 hexane/ethyl acetate) recovered 1H-indole-4-carbaldehyde (1) (500 mg) and gave 1-(pentan-2-yl)-1H-indole-4-carbaldehyde (3) mixed with residual 2-bromopentane (2), which was used in the following step directly.

1. temperaturethe reaction solution was warmed up to room temperature gradually
2. stirringstirred for 12 h at room temperature
3. customto quench
4. customthe reaction
5. washwashed with H2O (40 mL)
6. dry with materialThe organic layer was dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customPurification by flash chromatography (6:1 hexane/ethyl acetate)
10. customrecovered 1H-indole-4-carbaldehyde (1) (500 mg)