Chloride → (5-Methoxy-2-methyl-1H-indol-3-yl)(4-methylphenyl)methanone

Participants

Reaction Steps

To a solution of 5-methoxy-2-methylindole (816 mg, 5.06 mmol) in dichloromethane (15 ml) were added zinc chloride (1.52 g, 11.14 mmol) and ethyl magnesium bromide diethy ether (3.0 mol/l, 2.02 ml, 6.07 mmol) and the mixture was stirred for 1 hour at room temperature. Thereto was added p-toluoyl chloride (1.25 g, 8.10 mmol). After stirring for 1 hour, thereto was added alminium chloride (337 mg, 2.53 mmol) and the mixture was stirred at room temperature for 20 hours. To the reaction mixture was added an aqueous saturated ammonium chloride solution and the mixture was extracted with chloroform. The organic layer was washed with a saturated sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography and by recrystallization to give the subject compound (833 mg, 59%).

Provenance & Evidence