Tetrahydrofuran → 1H-indol-4-ylmethanol

Participants

Reaction Steps

To a solution of 6-indole carboxylic acid (500 mg, 3.1 mmol) in tetrahydrofuran (31 ml) is added lithium aluminum hydride (590 mg, 15.5 mmol) at 0° C. The reaction mixture is refluxed for 6 hours. The resulting mixture is then quenched with 5% potassium hydrogen sulfate (20 ml) and extracted with ether (20 mL). The organic layer is then dried with sodium sulfate and concentrated to give a yellow solid (230 mg). MS (ESI) m/z 146.6 (M+1).

Provenance & Evidence