Hydrochloric Acid → HCID 19024734, compound

Participants

Reaction Conditions

Reaction Steps

3-[2,2-Bis(4-isobutylphenyl)ethyl]benzoic acid (1 g) was converted to 3-[2,2-bis(4-isobutylphenyl)ethyl]benzoyl chloride (1.13 g) with oxalyl chloride as an usual manner. To a solution of indole (0.918 g) in tetrahydrofuran (15 ml) was added 3M solution of methyl magnesium bromide in ether (3 ml) at 20° C., and the mixture was stirred at 20° C. for 1 hour. A solution of 3-[2,2-bis(4-isobutylphenyl)ethyl]benzoyl chloride (1.13 g) in tetrahydrofuran (15 ml) was added to the mixture at 20° C. After stirred at 20° C. for 1 hour, the mixture was poured into a mixture of 1N-hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water, aqueous sodium bicarbonate and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (50 g) eluting with a mixture of hexane and ethyl acetate (20:1) to give 3-[3-[2,2-bis(4-isobutylphenyl)ethyl]benzoyl]indole (468 mg) as pale red crystals.

Provenance & Evidence