Реакция #95256

Уравнение реакции

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

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

acetone

water

→

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

Растворители

MeOH

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 ether
4. 4
   ЭкстракцияThe extract is extracted with half saturated sodium bicarbonate solutions
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

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 93) in 100 ml. of acetone and 65 ml. of water is added 8.80 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 ether. The extract is extracted with half saturated sodium bicarbonate solutions. The basic solutions 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; λmax.MeOH =233 mμ. (7360); νmax.=3380 (hydroxyl groups), 1710 (carbonyl groups), and 1632 cm-1 (olefin group).

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