반응 #157720

반응 방정식

Bromine

(5R)-5-[(Z)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one

→

title compound

수율 62.0%

(5R)-5-[(Z)-2-Bromo-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one

수율 62.0%

용매

carbon tetrachloride

반응 조건

후처리

1. 1
   온도cooling
2. 2
   농축The reaction solution was concentrated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in chloroform
4. 4
   workup.ADDITION1,8-Diazabicyclo[5.4.0]undec-7-ene (238 μL) was added under ice-
5. 5
   온도cooling
6. 6
   workup.STIRRINGthe mixture was stirred at room temperature for one hour
7. 7
   workup.ADDITIONThe reaction solution was poured into water
8. 8
   추출followed by extraction with ethyl acetate
9. 9
   세척The organic layer was washed with brine
10. 10
    건조dried over anhydrous magnesium sulfate
11. 11
    여과filtered
12. 12
    기타The solvent was then evaporated under reduced pressure
13. 13
    기타The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1)

실험 절차

Bromine (80 μL) was added to a solution of (5R)-5-[(Z)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one (200 mg) in carbon tetrachloride (2 mL) under ice-cooling, and the mixture was stirred at the same temperature (0° C.) for 15 minutes. The reaction solution was concentrated and the residue was dissolved in chloroform. 1,8-Diazabicyclo[5.4.0]undec-7-ene (238 μL) was added under ice-cooling, and the mixture was stirred at room temperature for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1) to give the title compound as a colorless powder (164 mg, 62%).

출처