Diethyl Ether → Indole-4-carboxaldehyde

Participants

Reaction Steps

Dess-Martin periodane (1.04 g, 2.46 mmol) was dissolved into anhydrous CH2Cl2 (10 ml). (1H-Indol-4-yl)-methanol (449 mg, 3.07 mmol) in anhydrous CH2Cl2 (10 ml) was added and the mixture was stirred for 1 h. Sodium hydroxide (50 ml of 1N solution) and ether (50 ml) were added and the reaction was stirred for 30 min. The organic layer was separated and washed with water (10 ml), brine (10 ml), dried over MgSO4, filtered and concentrated to a thick brown oil. Purification by column chromatography (silica gel, gradient elution of 2% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2) gave 1H-indole-4-carbaldehyde (235 mg, 53%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 11.59 (bs, 1H), 10.18 (s, 1H), 7.78-7.75 (m, 1H), 7.66-7.60 (m, 2H), 7.33-7.28 (m, 1H), 7.08 (d, J=3.0 Hz, 1H).

Provenance & Evidence