Sodium hydride → 1-[2-(tert-Butyldimethylsilyloxy)ethyl]-6-methoxy-1H-indole

Participants

Reaction Steps

To a solution of 6-methoxy-1H-indole (7.0 g, 47.6 mmol) and (2-bromoethoxy)-tert-butyldimethylsilane (10.7 mL, 50.0 mmol) in DMF (100 mL) under nitrogen was added, portionwise, sodium hydride (65% dispersion in oil) (2.8 g, 71.4 mmol) at room temperature. The reaction mixture was stirred for 1 h, quenched with saturated aq NaHCO3 (100 mL) and diluted with EtOAc (150 mL). The organic phase was washed with water (3×150 mL), saturated aq NaHCO3 (100 mL), brine (2×100 mL), dried (MgSO4), filtered and concentrated. Flash chromatography (SiO2, 10% EtOAc/hexanes) gave the title compound (14.8 g, 98%) as a colorless oil. 1H NMR (300 MHz, CDCl3) 7.62 (d, J=7.2 Hz, 1H), 7.38 (s, 1H), 7.12 (d, J=3.1 Hz, 1H), 6.87 (d, J=7.2 Hz, 1H), 6.52 (d, J=3.1 Hz, 1H), 4.28 (m, 2H), 4.02 (m, 2H), 3.96 (s, 3H), 0.98 (s, 9H), 0.02 (s, 6H).

Provenance & Evidence