(i) Preparation of tert-butyl-(2-iodoethoxy)dimethylsilane
To a stirred solution of 2-iodoethanol (17.2 g, 100 mmol) and imidazole (8.17 g, 120 mmol) in dichloromethane (100 mL) was slowly added tert-butyldimethylmethylsilyl chloride (15.83 g, 105 mmol) at a controlled rate of addition to maintain the reaction temperature at no more than 30 °C. The reaction was carried out by stirring the mixture for 17 hours. After addition, the reaction mixture was continued to be stirred for 17 hours. Upon completion of the reaction, the organic phase was washed sequentially with water (2 x 50 mL) and brine (50 mL), followed by drying with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford the colorless liquid-like product tert-butyl-(2-iodoethoxy)dimethylsilane (28.0 g, 97.8 mmol, 98% yield).
1H-NMR (400 MHz, CDCl3): δ = 3.83 (t, 2H, J = 7.0 Hz), 3.20 (t, 2H, J = 7.0 Hz), 0.90 (s, 9H), 0.08 (s, 6H) ppm.
