Dimethylformamide → 1H-Indole-6-carboxaldehyde

Participants

Reaction Steps

Potassium hexamethyldisilazane (0.5M in toluene) (56 ml) was added dropwise to a ice cold solution of 6-bromoindole (5.0 g) in diethyl ether (50 ml). The reaction mixture was warmed to room temperature for 30 mins and then cooled to −78° C. tBuLi (1.7M) (31.5 ml) was added to the mixture keeping the temperature below −65° C. the mixture was further stirred at −78° C. for 30 mins after which time a solution of DMF (6 ml) in diethyl ether (10 ml) was added, the reaction mixture was warmed to room temperature and quenched with ice cold 2N HCl the product was then extracted into diethyl ether (×3). The combined organic layers were dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with Dichloromethane/Methanol (97/3, v/v) to afford the title compound as a solid (1.49 g).

Provenance & Evidence