Reaction Steps
At −78° C., a 1.6 M solution of butyllithium (30 mL, 48 mmol) in hexane was added to a solution of 2-bromophenylmethanol (3.7 g, 20 mmol) in THF, and the resulting mixture was stirred at −78° C. for 1.5 hours. At −78° C., chloro(dimethyl)vinylsilane (7.2 g, 60 mmol) was added to the reacted mixture, and the resulting mixture was stirred for two hours. The resulting mixture solution was diluted with diethyl ether, and was washed with water and brine, and then was dried over anhydrous MgSO4. After removal of the solvents under reduced pressure, the residue was purified by flash chromatography on silica gel, thereby obtaining [2-(hydroxymethyl)phenyl]dimethyl(vinyl)silane: 1h (3.1 g, yield of 80%) as a colorless oil, Rf: 0.30 (hexane-ethyl acetate=7:1). 1H NMR (400 MHz, CDCl3) δ 7.56 (dd, J=7.3, 1.3 Hz, 1H), 7.46 (dd, J=7.1, 0.7 Hz, 1H), 7.41 (td, J=7.4, 1.5 Hz, 1H), 7.30 (td, J=7.3, 1.5 Hz, 1H), 6.39 (dd, J=20.3, 14.6 Hz, 1H), 6.08 (dd, J=14.6, 3.7 Hz, 1H), 5.79 (dd, J=20.3, 3.7 Hz, 1H), 4.74 (s, 2H), 1.71 (br s, 1H), 0.43 (s, 6H); 13C NMR (101 MHz, CDCl3) δ 146.4, 139.0, 136.2, 135.2, 132.8, 129.8, 128.0, 127.0, 65.3, −1.6; Anal. Calcd for C11H16Osi; C, 68.69; H, 8.39. Found: C, 68.43; H, 8.36.
