반응 #8312

반응 방정식

1-(2-pyridyl)-2-(4-quinolyl)ethan-1-one

triethylamine

Trifluoromethanesulfonic anhydride

triphenyphosphine oxide

→

title compound

수율 43.4%

4-(2-(2-Pyridyl)ethynyl)quinoline

수율 43.4%

용매

1,2-dichloroethane

1,2-dichloroethane

반응 조건

후처리

1. 1
   온도is cooled in an ice bath
2. 2
   기타The ice bath is removed
3. 3
   온도the mixture heated
4. 4
   온도at reflux for 16 h
5. 5
   workup.ADDITIONThe mixture is diluted with dichloromethane (100 mL)
6. 6
   세척washed with water (3×100 mL)
7. 7
   건조dried (magnesium sulfate)
8. 8
   여과filtered
9. 9
   농축concentrated in vacuo
10. 10
    기타chromatographed on SiO2 (0 to 100% hexane in ethyl acetate)

실험 절차

A mixture of triphenyphosphine oxide (5.56 g, 10 mmol) in 1,2-dichloroethane (30 mL) is cooled in an ice bath. Trifluoromethanesulfonic anhydride (1.57 mL, 10 mmol) is added dropwise over 15 min. To this mixture is added a solution of 1-(2-pyridyl)-2-(4-quinolyl)ethan-1-one (2.5 g, 10 mmol) in 1,2-dichloroethane (10 mL) and triethylamine (2.84 mL, 20 mmol). The ice bath is removed and the mixture heated at reflux for 16 h. The mixture is diluted with dichloromethane (100 mL) and washed with water (3×100 mL), dried (magnesium sulfate), filtered, concentrated in vacuo, and chromatographed on SiO2 (0 to 100% hexane in ethyl acetate) to yield 1 g of title compound as an oil.

출처