4-Toluenesulfonyl chloride → 1-(4-Methylbenzene-1-sulfonyl)-1H-indole-3-carbaldehyde

Participants

Reaction Steps

To a solution of 1H-indole-3-carboxaldehyde (300 mg, 2.07 mmol) in 6.2 mL of dry dimethylsulfoxide was added sodium hydride (108 mg, 55%, 2.5 mmol) under nitrogen at 0° C. After the reaction mixture was stirred for 30 min at room temperature, p-toluenesulfonyl chloride (434 mg, 2.28 mmol) was added with additional stirring for 1 h. The reaction mixture was diluted with 10 mL of ethyl acetate and 10 mL of saturated NH4Cl aqueous solution, successively, and the solution was extracted with 100 mL of ethyl acetate. The extract was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4 After filtration, the solution was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40) to obtain the title compound as a pale yellow solid (310 mg, 50%).

Provenance & Evidence