Tetrahydrofuran → 6-Hydroxymethylindole

Participants

Reaction Conditions

Reaction Steps

Indole-6-carboxylic acid (1.0 g, 6.2 mmol) was dissolved into anhydrous THF (20 mL) under argon. Lithium aluminum hydride (494 mg, 13 mmol) was added portionwise and the mixture was stirred overnight. The mixture was cooled to 0° C. and ethyl acetate (10 mL) was carefully added, followed by methanol (5 mL) and water (5 mL). The mixture was stirred for 30 min. and filtered through celite. The solution was concentrated and dissolved into ethyl acetate (200 mL) and washed with brine (2×20 mL), dried over MgSO4 and concentrated to afford the title compound as a brown oil (880 mg, 96%). 1H NMR (300 MHz, CDCl3) δ 8.30 (s, 1H), 7.58 (d, J=8.1 Hz, 1H), 7.23 (d, J=1.1 Hz, 1H), 7.13-7.05 (m, 2H), 6.51-6.49 (m, 1H), 4.70 (s, 2H).

Provenance & Evidence