反应详情

温度

-78 °C

To a solution of 2-(4-bromophenyl)-1,3-dioxolane (2 Scheme 18, 6.0 g, 26.2 mmol) in dried THF (200 mL) at −78° C. was added t-butyllithium (15.4 mL, 1.7 M solution in pentane, 26.2 mmol) over a period of 5 min. After 30 min of further stirring at −78° C., allylchlorodimethylsilane (3.7 g, 27.5 mmol) in THF (20 mL) was added dropwise over a period of 10 min. The reaction mixture was stirred for 1 h and warmed to room temperature. THF was removed under reduced pressure, and the residue was extracted with cold water/ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), and concentrated to give a colorless oil (5.4 g, 91%); 1H NMR (300 MHz, CDCl3) δ 0.31 (s, 6 H), 1.78 (d, J=7.95 Hz, 2 H), 4.02-4.18 (4 H), 4.85 (s, 1 H), 4.90 (m, 1 H), 5.78 (m, 1 H), 5.85 (s, 1 H), 7.50 (d, J=7.95 Hz, 2 H), 7.58 (d, J=7.95 Hz, 2 H); 13C NMR (75 MHz, CDCl3) −3.4 (2C), 23.7, 65.4 (2C), 103.7, 113.6, 125.8 (2C), 133.8 (2C), 134.6, 138.8, 139.9; HRMS calcd for C14H20O2Si 248.1233, found 248.1230.

1. stirringThe reaction mixture was stirred for 1 h
2. temperaturewarmed to room temperature
3. customTHF was removed under reduced pressure
4. extractionthe residue was extracted with cold water/ethyl acetate
5. washThe organic layer was washed with brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated