تفاعل #8312

معادلة التفاعل

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

triethylamine

Trifluoromethanesulfonic anhydride

triphenyphosphine oxide

→

title compound

المردود 43.4%

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

المردود 43.4%

المذيبات

1,2-dichloroethane

1,2-dichloroethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةis cooled in an ice bath
2. 2
   أخرىThe ice bath is removed
3. 3
   درجة الحرارةthe mixture heated
4. 4
   درجة الحرارةat reflux for 16 h
5. 5
   workup.ADDITIONThe mixture is diluted with dichloromethane (100 mL)
6. 6
   غسيلwashed with water (3×100 mL)
7. 7
   تجفيفdried (magnesium sulfate)
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated in vacuo
10. 10
    أخرىchromatographed on SiO2 (0 to 100% hexane in ethyl acetate)

الإجراء التجريبي

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.

المصدر