反応 #8312

反応方程式

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

triethylamine

Trifluoromethanesulfonic anhydride

triphenyphosphine oxide

→

title compound

収率 43.4%

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

収率 43.4%

溶媒

1,2-dichloroethane

1,2-dichloroethane

反応条件

後処理

1. 1
   温度is cooled in an ice bath
2. 2
   その他The ice bath is removed
3. 3
   温度the mixture heated
4. 4
   温度at reflux for 16 h
5. 5
   workup.ADDITIONThe mixture is diluted with dichloromethane (100 mL)
6. 6
   洗浄washed with water (3×100 mL)
7. 7
   乾燥dried (magnesium sulfate)
8. 8
   ろ過filtered
9. 9
   濃縮concentrated in vacuo
10. 10
    その他chromatographed on SiO2 (0 to 100% hexane in ethyl acetate)

実験手順

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.

出典