Water → 4-Iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazole

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Reaction Steps

To a stirring solution of 4-iodo-1H-benzimidazole (1.00 g, 4.1 mmol) in DMF (12 mL) was added sodium hydride (180 mg of a 60% dispersion in mineral oil; 4.5 mmol), and the resulting mixture was stirred at room temperature under nitrogen for 50 minutes. 2-(Trimethylsilyl)ethoxymethyl chloride (870 μL, 4.92 mmol) was added dropwise over 5 minutes at room temperature, then the mixture was stirred overnight. Water (50 mL) was added, and the mixture was washed with ethyl acetate (3×25 mL). The combined organic layers were washed with water (2×30 mL), then with saturated sodium chloride solution (30 mL), then dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel, eluting with 0 to 20% ethyl acetate in dichloromethane, affording the product as a white solid (1.20 g, 78%). 1H NMR (400 MHz, CDCl3): δ 8.05 (1H, s), 7.74 (1H, dd, J=0.6, 7.5 Hz), 7.52 (1H, t, J=4.2 Hz), 7.09 (1H, t, J=7.9 Hz), 5.51 (2H, s), 3.50 (2H, t, J=8.2 Hz), 0.90 (2H, dd, J=8.3, 16.4 Hz), −0.05 (9H, s); m/z (ES+) 375 [MH+].

Provenance & Evidence