Sodium Hydroxide → 1H-Indole-6-carboxaldehyde

Participants

Reaction Steps

Dess-Martin periodinane (1.53 g, 2.6 mmol) was dissolved into methylene chloride (15 mL). Indol-6-yl-methanol (500 mg, 3.4 mmol) in methylene chloride (12 mL) was added and the mixture was stirred for 1 hr. Sodium hydroxide (5 mL of 1 N solution) was added and the reaction was stirred for 15 min. The organic layer was separated and washed with H2O (5 mL), brine (5 mL), dried over MgSO4 and concentrated to afford the title compound as a brown solid (275 mg, 56%). 1H NMR (300 MHz, DMSO-d6) δ 11.7 (s, 1H), 9.98 (s, 1H), 7.97 (s, 1H), 7.70-7.65 (m, 2H), 7.52 (dd, J=8.2, 1.4 Hz, 1H), 6.57-6.5 (m, 1H).

Provenance & Evidence