Methyl iodide → 4-Methoxy-1-methylindole

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methoxy-1H-indole (CAS#4837-90-5, 4.0 g, 27.2 mmol) in THF (100 ml) at 0° C. was added sodium hydride (60% dispersion in oil, 1.63 g, 40.08 mmol). The reaction was stirred for 15 minutes at 0° C. and then put at room temperature for 1 h. The reaction was then re-cooled to 0° C. and iodomethane (2.209 ml, 35.3 mmol) was added. The reaction was then put at room temperature and permitted to stir for 45 minutes. The reaction was then quenched with saturated aqueous ammonium chloride and concentrated to approximately half of its original volume. Next, the reaction mixture was diluted with water and dichloromethane and the layers were separated. The aqueous layer was then extracted two additional times with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane 0 to 30%) to afford 4-methoxy-1-methyl-1H-indole; MS: (ES+) m/z 162.0 (M+H)+.

Provenance & Evidence