Sodium Hydroxide → HCID 86040275, compound

Participants

Reaction Steps

To a solution of 1-benzyl-1H-indole-3-carbaldehyde (1.086 g, 4.61 mmol) in 4:1 ethanol:2.5 M NaOH solution (16 mL) was added O-allyl hydroxylamine hydrochloride hydrate(0.768 g, 7.17 mmol). The reaction mixture was heated to reflux for 30 minutes and allowed to cool back down to room temperature. The reaction mixture was concentrated to a small volume and the pH of the mixture was then adjusted to 7 using 2 M hydrochloric acid. The mixture was extracted with ethyl acetate. The combined organics were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude oil was purified by flash chromatography through silica gel using ethyl acetate/hexanes (10/90) to give 1-benzyl-1H-indole-3-carbaldehyde O-allyl-oxime (0.176 g, 88%) as a colorless oil. 1H NMR (400 MHz, CDCl3); δ 8.30(s, 1H), 8.15 (m, 1H), 7.24 (m, 7H), 7.10 (d, 2H), 6.10 (m, 1H), 5.30 (m, 4H), 4.68 (d, 2H).

Provenance & Evidence