Methyl iodide → 1-Methyl-1H-indole-4-carbaldehyde

Participants

Reaction Steps

To a solution of 1H-indole-4-carbaldehyde (0.252 g, 1.72 mmol) in 8 mL of DMF was added sodium hydride (0.046 g, 1.9 mmol). After 5 min, iodomethane (0.13 mL, 2.1 mmol) was added. After 30 min, the reaction was treated with saturated aqueous ammonium chloride, diluted with water, and extracted 2× with dichloromethane. The combined organic fractions were washed 3× with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-40% ethyl acetate in hexanes to provide 1-methyl-1H-indole-4-carbaldehyde that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 161.2 for [M+H]+.

Provenance & Evidence