Imidazole → HCID 21950027, compound

Participants

Reaction Steps

To a solution of 7-hydroxypropyl-1H-indole (4.45 g, 25.4 mmol) in methylene chloride (50 mL), was added imidazole (2.31 g, 34.0 mmol), followed by tert-butyldimethylsilyl chloride (5.44 g, 36.1 mmol). The reaction mixture was stirred at room temperature for 12 h, filtered and concentrated to a brown oil. Flash chromatography (SiO2, 10% EtOAc/hexanes) gave the title compound (4.9 g, 66%) as a colorless oil. 1H NMR (300 MHz, CDCl3) 9.38 (bs, 1H), 7.54 (m, 1H), 7.22 (m, 1H), 7.18–6.06 (m, 2H), 6.60 (m, 1H), 3.71 (m, 2H), 3.07 (m, 2H), 1.98 (m, 2H), 1.03 (s, 9H), 0.20 (s, 6H).

Provenance & Evidence