Methyl iodide → 4-(Benzyloxy)-1-methyl-1H-indole

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-benzyloxy-1H-indole (CAS#20289-26-3, 10.85 g, 48.6 mmol) in N,N-dimethylformamide (200 mL) at 0° C., was added sodium hydride (60% dispersion in oil, 2.24 g, 55.9 mmol). The reaction was permitted to stir for 15 minutes at 0° C. Then iodomethane (3.19 mL, 51.0 mmol) was added to the reaction mixture. The reaction was put at room temperature and permitted to stir 30 minutes. The reaction was then quenched with saturated aqueous ammonium chloride. The mixture was diluted with water and extracted with diethyl ether. The layers were separated and the aqueous layer was then extracted two additional times with diethyl ether. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 4-benzyloxy-1-methyl-1H-indole; MS: (ES+) m/z 238.4 (M+H)+.

Provenance & Evidence