Reaktion #1244298

Reaktionsgleichung

cyclooctanone

triethylamine

chlorotrimethylsilane

→

desired product

Ausbeute 93.0%

(Cyclooct-1-enyloxy)-trimethylsilane

Ausbeute 93.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated to reflux
2. 2
   Sonstigethe reaction was quenched with 20 mL of H2O
3. 3
   Sonstigethe DMF was removed on a rotary evaporator
4. 4
   workup.ADDITIONThe residue was diluted with hexanes (300 mL)
5. 5
   Waschenwashed with H2O (3×100 mL) and brine (1×50 mL)
6. 6
   Trocknendried over MgSO4
7. 7
   workup.DISTILLATIONDistillation under reduced pressure (20 torr)

Vorschrift

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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