Reaktion #7910

Reaktionsgleichung

(4-chlorophenyl)acetonitrile

2-bromoethyl ether

dimethylsulfoxide

sodium hydride

→

4-(4-chlorophenyl)tetrahydropyran-4-carbonitrile

Ausbeute 95.5%

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a round-bottom flask under argon fitted with an addition funnel
2. 2
   Temperaturwhile maintaining the reaction temperature at 20–30° C
3. 3
   SonstigeThe reaction mixture was carefully quenched with water (50 mL)
4. 4
   Extraktionextracted with hexane (3×100 mL)
5. 5
   Waschenwashed with water (3×75 mL), brine (50 mL)
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   Sonstigeto give a pale yellow oil
10. 10
    SonstigeThe oil was purified by column chromatography on silica gel

Vorschrift

Into a round-bottom flask under argon fitted with an addition funnel and thermometer was added anhydrous dimethylsulfoxide (60 mL) and sodium hydride (1.17 g, 48.8 mmol, 95%). Then a solution of (4-chlorophenyl)acetonitrile (G) (3.37 g, 22.2 mmol) and 2-bromoethyl ether (90%, 3.41 mL, 24.4 mmol) in diethyl ether (15 mL) was added slowly, while maintaining the reaction temperature at 20–30° C. The reaction mixture was maintained at room temperature for overnight. The reaction mixture was carefully quenched with water (50 mL) and then extracted with hexane (3×100 mL). The organic extracts were combined, washed with water (3×75 mL), brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated to give a pale yellow oil. The oil was purified by column chromatography on silica gel using hexane/ethyl acetate (80:20) to give 4.7 g of 4-(4-chlorophenyl)tetrahydropyran-4-carbonitrile, H, as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 2.00–2.15 (m, 4H); 3.89 (dt, 2H, J=12.6 Hz, J2=3 Hz); 4.05–4.11 (m, 2H); 7.37–7.45 (m, 4H); 13C NMR (CDCl3, 75 MHz): δ 36.66 (2C), 41.51, 64.98 (2C), 121.40, 127.03, 129.37, 134.31, 138.46.

Quelle