Reaktion #216973

Reaktionsgleichung

tert-Butyllithium

4-bromodiphenyl ether

acrolein

→

title compound

Ausbeute 73.0%

α-Ethenyl-4-phenoxybenzenemethanol

Ausbeute 73.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe cooling bath was removed
2. 2
   workup.STIRRINGThe colorless reaction mixture was stirred at 0° C. for 15 min
3. 3
   Sonstigequenched by addition of saturated NH4Cl (10 mL)
4. 4
   workup.ADDITIONThe mixture was diluted with diethyl ether (200 mL)
5. 5
   Waschenthe organic layer was washed with water (20 mL) and brine (50 mL)
6. 6
   Trocknendried over MgSO4
7. 7
   SonstigeEvaporation
8. 8
   Sonstigegave a crude oil which
9. 9
   Sonstigewas purified by flash chromatography on silica gel (400 g)
10. 10
    Wascheneluted with a step gradient of 10:90 EtOAc/hexane to 15:85 EtOAc/hexane to 20:80 EtOAc/hexane

Vorschrift

tert-Butyllithium (24.5 mL, 1.7M in pentane, 42.2 mmol) was added dropwise over 30 min to a solution of 4-bromodiphenyl ether (5.00 g, 20.1 mmol) in THF (50 mL) at -78° C. under argon. The cooling bath was removed and the bright yellow reaction mixture was warmed to 0° C. over 20 min. The reaction was stirred at 0° C. for 30 min, at which time a tan-colored solution developed. Freshly distilled acrolein (1.6 mL, 24 mmol) was added dropwise over 5 min. The colorless reaction mixture was stirred at 0° C. for 15 min, then quenched by addition of saturated NH4Cl (10 mL). The mixture was diluted with diethyl ether (200 mL) and the organic layer was washed with water (20 mL) and brine (50 mL), then dried over MgSO4. Evaporation gave a crude oil which was purified by flash chromatography on silica gel (400 g) eluted with a step gradient of 10:90 EtOAc/hexane to 15:85 EtOAc/hexane to 20:80 EtOAc/hexane to provide title compound (3.31 g, 73%) as a colorless oil.

Quelle