反应 #1244298

反应方程式

cyclooctanone

triethylamine

chlorotrimethylsilane

→

desired product

收率 93.0%

(Cyclooct-1-enyloxy)-trimethylsilane

收率 93.0%

溶剂

DMF

反应条件

后处理

1. 1
   温度The reaction was heated to reflux
2. 2
   其他the reaction was quenched with 20 mL of H2O
3. 3
   其他the DMF was removed on a rotary evaporator
4. 4
   workup.ADDITIONThe residue was diluted with hexanes (300 mL)
5. 5
   洗涤washed with H2O (3×100 mL) and brine (1×50 mL)
6. 6
   干燥dried over MgSO4
7. 7
   workup.DISTILLATIONDistillation under reduced pressure (20 torr)

实验过程

To a solution of cyclooctanone (40.0 g, 316 mmol) in 200 mL of anhydrous DMF were added triethylamine (TEA, 93.0 mL, 666 mmol) and chlorotrimethylsilane (84.0 mL, 666 mmol). The reaction was heated to reflux. After 15 h, the reaction was quenched with 20 mL of H2O and the DMF was removed on a rotary evaporator. The residue was diluted with hexanes (300 mL), washed with H2O (3×100 mL) and brine (1×50 mL), and dried over MgSO4. Distillation under reduced pressure (20 torr) yielded 58.1 g (93%) of the desired product as a colorless oil, bp 108° C. (20 torr) (lit. 106° C. at 25 torr). Nakamura, et al. J. Am. Chem. Soc. (1976) 98, 2346-2348. IR: 2926, 2851, 1661 cm−1. 1H NMR (CDCl3, 300 MHz): δ 0.20 (s, 9H), 1.39-1.58 (m, 8H), 2.02 (m, 2H), 2.19 (m, 2H), 4.75 (t, 1H, J=9.0 Hz). (Lit: 1H NMR (CDCl3, 600 MHz): δ 0.16 (s, 9H), 1.46 (m, 4H), 1.49 (m, 2H), 1.55 (m, 2H), 1.97 (m, 2H), 2.14 (m, 2H), 4.70 (t, 1H, J=8.0 Hz) (Frimer et al. J. Org. Chem. (2000) 65, 1807-1817.) 13C NMR (CDCl3, 75 MHz): δ 0.4, 25.5, 26.3, 26.4, 27.8, 30.9, 31.0, 105.41, 152.99. (Lit: 13C NMR (CDCl3, 150 MHz): δ 0.45, 25.52, 26.36, 26.40, 27.83, 30.98, 31.05, 105.45, 153.05) Frimer et al. (2000) supra) FAB—HRMS: Calcd. for C11H23OSi+[M+H]+: 199.1518, found 199.1520.

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