Reacción #8312

Ecuación de reacción

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

triethylamine

Trifluoromethanesulfonic anhydride

triphenyphosphine oxide

→

title compound

Rendimiento 43.4%

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

Rendimiento 43.4%

Disolventes

1,2-dichloroethane

1,2-dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturais cooled in an ice bath
2. 2
   OtroThe ice bath is removed
3. 3
   Temperaturathe mixture heated
4. 4
   Temperaturaat reflux for 16 h
5. 5
   workup.ADDITIONThe mixture is diluted with dichloromethane (100 mL)
6. 6
   Lavadowashed with water (3×100 mL)
7. 7
   Secadodried (magnesium sulfate)
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated in vacuo
10. 10
    Otrochromatographed on SiO2 (0 to 100% hexane in ethyl acetate)

Procedimiento

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.

Fuente