Реакция #319107

Уравнение реакции

7-(2,5-dioxocyclopentyl) heptanoic acid

triphenyl phosphine

bromine

triethyl amine

→

7-(2-bromo-5-oxo-1-cyclopentenyl) heptanoic acid

Выход 67.0%

Растворители

water

benzene

benzene

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe mixture was stirred for 10 minutes at room temperature
2. 2
   Другоеat 0° C
3. 3
   workup.STIRRINGThe mixture was stirred for 26 hours
4. 4
   ЭкстракцияThe aqueous solution was extracted with three 20 ml portions of ether
5. 5
   ПромывкаThe ether layer was washed with water and saturated aqueous sodium chloride solution
6. 6
   Сушкаdried over anhydrous magnesium sulfate
7. 7
   ДругоеThe reaction mixture was purified by thin layer chromatography

Методика

A dried triphenyl phosphine (288 mg) was dissolved in a dried benzene (10 ml), and then 1M bromine in benzene solution (1.1 ml) was added thereto while stirring at 0° C. over 3 minutes. The mixture was stirred for 10 minutes at room temperature, and then dried triethyl amine (0.15 ml) was added thereto at 0° C. Continuously, 7-(2,5-dioxocyclopentyl) heptanoic acid (113 mg) were added thereto. The mixture was stirred for 26 hours, and poured into the same volume of water. The aqueous solution was extracted with three 20 ml portions of ether. The ether layer was washed with water and saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The reaction mixture was purified by thin layer chromatography to afford 7-(2-bromo-5-oxo-1-cyclopentenyl) heptanoic acid (yield 96.6 mg, 67%).

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