Реакция #157720

Уравнение реакции

Bromine

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

→

title compound

Выход 62.0%

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

Выход 62.0%

Растворители

carbon tetrachloride

Условия реакции

Обработка

1. 1
   Температураcooling
2. 2
   КонцентрированиеThe 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
   Температураcooling
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
   Экстракцияfollowed by extraction with ethyl acetate
9. 9
   ПромывкаThe organic layer was washed with brine
10. 10
    Сушкаdried over anhydrous magnesium sulfate
11. 11
    Фильтрацияfiltered
12. 12
    ДругоеThe solvent was then evaporated under reduced pressure
13. 13
    ДругоеThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1)

Методика

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%).

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