Hexane → HCID 11415144, compound

Participants

Reaction Steps

Under nitrogen, to a stirred solution of ethyl 3-(5-benzyloxy-1-methylindol-3-yl)propionate (12.0 g, 35.6 mmol) in dichloromethane (120 ml) was added dropwise 1.0 M DIBAL in hexane (37.4 ml, 35.6 mmol) at −78° C. (dry-ice/acetone) for 25 minutes. After 30 minutes, methanol (5.7 ml) was added dropwise at −78° C. and then the mixture was stirred at room temperature for 30 minutes. The mixture was filtered through Celite and washed with dichloromethane. The filtrate was concentrated in vacuo and then the residue was purified by silica gel (90 g) chromatography eluted with toluene/ethyl acetate (10:1 to 5:1) to give 3-(5-benzyloxy-1-methylindol-3-yl)propionaldehyde (8.03 g, 77.0%)

Provenance & Evidence