Hydrochloric Acid → HCID 10705928, compound

Participants

Reaction Conditions

Reaction Steps

Boron trifluoride etherate (4.2 ml) was added to a mixture of methyl 4-(5-chloroindol-3-yl)-4-oxobutyrate (3.00 g) and sodium borohydride (0.855 g) in tetrahydrofuran (100 ml) at 25° C. over 20 minutes. After the mixture was stirred at 25° C. for 3 hours, acetone (5 ml) was added. The reaction mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of solvent, the residue was purified by column chromatography on silica gel (200 ml) eluting with chloroform and by recrystallization from a mixture of ethyl acetate and hexane to give methyl 4-(5-chloroindol-3-yl)butyrate (989 mg) as colorless crystals.

Provenance & Evidence