Sodium hydride → HCID 67044778, compound

Participants

Reaction Steps

To a suspension of sodium hydride (0.27 g, 6.6 mmol) in tetrahydrofuran (10 mL) at 0° C. was added 5-bromoindole (1.0 g, 5.1 mmol). The reaction was stirred for 30 min at room temperature, then cooled to 0° C. and 2-(trimethylsilyl)ethoxymethyl chloride (1.0 mL, 5.6 mmol) was added. The solution was stirred for 2 h at room temperature. The reaction mixture was poured into saturated aqueous ammonium chloride solution and diluted with ether. The layers were separated and the aqueous layer was extracted (2×100 mL ether). The combined organic layers were washed with brine, dried (magnesium sulfate), filtered and concentrated in vacuo. Column chromatography (silica gel, 20:1 hexanes/ethyl acetate) gave 1.1 g (66%) of 5-bromo-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-indole. 1H NMR (400 MHz, CDCl3): 7.81 (d, 1H), 7.42 (d, 1H), 7.38 (dd, 1H), 7.23 (d, 1H), 6.52 (dd, 1H), 5.51 (s, 2H), 3.60 (m, 2H), 0.93 (m, 2H), 0.00 (s, 9H); MS (EI) for C14H20NOSiBr: 209 (M−OCH2CH2Si(CH3)3).

Provenance & Evidence