Benzyl Bromide → HCID 18973498, compound

Participants

Reaction Steps

There was suspended 26.4 mg of 60% sodium hydride in 5 ml of dimethylformamide, followed by addition of a solution of 1-(2-hydroxy-2-phenylethyl)indole-4-carbaldehyde (160 mg) in dimethylformamide (2 ml) with ice-cooling. After stirring at room temperature for 15 minutes, the mixture was ice-cooled, then a solution of benzyl bromide (115.2 mg) in dimethylformamide (2 ml) was added thereto and stirred at room temperature for 3 hours. The reaction system was poured into 50 ml of a 10% ammonium chloride aqueous solution and extracted with ethyl acetate (50 ml×2). The resulting organic phase was washed with, in order, a 10% citric acid aqueous solution, a saturated sodium hydrogen carbonate aqueous solution and a saturated common salt solution, dried over anhydrous sodium sulfate and the solvent was removed through evaporation under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 170 mg of 1-(2-benzyloxy-2-phenylethyl)indole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 80%.

Provenance & Evidence