Dimethylformamide → 1-Benzothiophene-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of benzothiophene (2 g, 14.9 mmol) in 100 mL of THF cooled to −78° C. was added 1.6 M n-butyl lithium in hexanes (10.25 mL, 16.39 mmol). The mixture was stirred at −78° C. for 1 h, warmed to 0° C., stirred for 5 min, recooled to −78° C. and treated with DMF (4.62 mL, 59.61 mmol). The temperature was allowed to rise slowly overnight. The reaction was quenched with saturated aqueous ammonium chloride and extracted with diethyl ether. The combined organic extracts were washed with water and brine, dried over MgSO4 and concentrated to afford the title compound as an oil. (2.216 g, 91%).

Provenance & Evidence