반응 #216973

반응 방정식

tert-Butyllithium

4-bromodiphenyl ether

acrolein

→

title compound

수율 73.0%

α-Ethenyl-4-phenoxybenzenemethanol

수율 73.0%

용매

THF

반응 조건

후처리

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

실험 절차

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.

출처