反应详情

温度

0 °C

To the crude chloro(4-methoxyphenyl)diisopropylsilane (54.8 g, 214 mmol, 1.0 equiv.) was added THF (335 mL) via cannula under positive argon pressure. The solution was chilled to 0° C. and treated with allylmagnesiumchloride (128 mL, 256 mmol, 2.0 M in THF, 1.2 equiv.). After 3 h at 0° C., the solution was allowed to warm to 23° C. with stirring overnight. The mixture was treated with NH4Clsat'd (50 mL) and the aqueous layer extracted with ether (3×500 mL). The combined organic extracts were washed with brine, dried (MgSO4), filtered, concentrated in vacuo. The crude material was purified by silica gel chromatography (3-5% EtOAc/hexanes) to yield 52.86 g (94%) of a slightly cloudy, viscous oil. This reagent distills at 130° C. at 500 mtorr as a colorless oil. TLC Rf=0.40 (9:1 Hexanes/EtOAc). IR (film) 2942, 2865, 1630, 1595, 1504, 1463, 1277 cm−1. 1H NMR (500 MHz, CDCl3) δ7.32 (d, 2H, J=6.84, C3-H,C7-H), 6.18 (d, 2H, J=6.84, C4-H, C6-H), 5.82 (q, 1H, J=8.5, 8.5, C15-H), 4.88 (d, 1H, J=17.05, C16-Hb), 4.76 (d, 1H, J=9.77, C16-Ha), 1.82 (d, 2H, J=7.32, C14-H), 1.17 (q, 2H, J=7.3, C8-H, C11-H), 0.94 (d, 6H, J=7.3, C9-H, C10-H), 0.90 (d, 6H, J=7.3, C12-H, C13-H). 13C NMR (125 MHz, CDCl3) δ160.51, 136.48, 135.70, 125.78, 113.78, 113.62, 55.09, 19.34, 18.22, 18.17, 17.68, 11.30. Anal. Calcd for C16H26OSi: C, 73.22; H, 9.98; Si, 10.70.

1. temperatureto warm to 23° C.
2. additionThe mixture was treated with NH4Clsat'd (50 mL)
3. extractionthe aqueous layer extracted with ether (3×500 mL)
4. washThe combined organic extracts were washed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude material was purified by silica gel chromatography (3-5% EtOAc/hexanes)
9. customto yield 52.86 g (94%) of a slightly cloudy, viscous oil
10. distillationThis reagent distills at 130° C. at 500 mtorr as a colorless oil