Water → 1-(pentan-2-yl)-1H-indole-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence