Реакция #157725

Уравнение реакции

(5R)-1-(2,4-Dimethoxybenzyl)-5-ethynylpyrrolidin-2-one

4-tert-butyliodobenzene

water

→

(5R)-5-[(4-tert-butylphenyl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

Выход 84.0%

Растворители

triethylamine

Условия реакции

Обработка

1. 1
   workup.WAITover one hour
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for three hours
3. 3
   Экстракцияfollowed by extraction with ethyl acetate
4. 4
   ПромывкаThe organic layer was washed with brine
5. 5
   Сушкаdried over anhydrous magnesium sulfate
6. 6
   Фильтрацияfiltered
7. 7
   ДругоеThe solvent was then evaporated under reduced pressure
8. 8
   ДругоеThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→1:1)

Методика

Copper iodide (74 mg) and bis(triphenylphosphine)palladium(II) dichloride (135 mg) were added to a solution of 4-tert-butyliodobenzene (3.0 g) in triethylamine (10 mL), and the mixture was stirred at room temperature for 15 minutes. (5R)-1-(2,4-Dimethoxybenzyl)-5-ethynylpyrrolidin-2-one (1.0 g) was added thereto over one hour, and the mixture was stirred at room temperature for three hours. 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=1:0→1:1) to give (5R)-5-[(4-tert-butylphenyl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one as a colorless powder (1.25 g, 84%).

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