Реакция #349094

Уравнение реакции

4-bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one

acetone

→

2-(6-carboxyhexyl)-4-hydroxy-cyclopent-2-en-1-one

Растворители

water

Условия реакции

Обработка

1. 1
   ТемператураThe temperature is maintained at 25°-30° C. by external cooling
2. 2
   Фильтрацияfiltered, saturated with sodium chloride
3. 3
   Экстракцияextracted with half saturated sodium bicarbonate solution
4. 4
   ЭкстракцияThe basic extract
5. 5
   Экстракцияextracted with ether
6. 6
   ПромывкаThe extract is washed with water and saturated sodium chloride solution
7. 7
   Сушкаdried over magnesium sulfate
8. 8
   Концентрированиеconcentrated
9. 9
   ДругоеThe crude product is purified
10. 10
    Другоеby partition chromatography on Celite
11. 11
    Другоеto give an oil with the properties

Методика

To a stirred solution of 10.6 g. (ca. 34 mmoles) of crude 4-bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one (Example 8) in 100 ml. of acetone and 65 ml. of water is added 8.0 g. (45.2 mmoles) of silver fluoborate during 2 minutes. The temperature is maintained at 25°-30° C. by external cooling. The mixture is stirred for 90 minutes, filtered, saturated with sodium chloride and extracted with half saturated sodium bicarbonate solution. The basic extract is reacidified with dilute hydrochloric acid, saturated with sodium chloride, and extracted with ether. The extract is washed with water and saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The crude product is purified by partition chromatography on Celite to give an oil with the properties described in Example 27.

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