1H-indole-6-carboxylic acid → 6-Hydroxymethylindole

Participants

Reaction Steps

To a solution of 6-indole carboxylic acid (5 g, 31.05 mmol) in tetrahydrofuran (310 ml) is added lithium aluminum hydride (5.89 mg, 155.2 mmol) at 0° C. The reaction mixture is refluxed for 6 hours. The resulting mixture is then quenched with 5% potassium hydrogen sulfate (100 ml) and extracted with ether (100 mL). The organic layer is then dried with sodium sulfate and concentrated to give a white solid (156 mg) MS (ESI) m/z 148.8 (M+1).

Provenance & Evidence