반응 #95256

반응 방정식

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

용매

MeOH

반응 조건

후처리

1. 1
   온도The temperature is maintained at 25°-30° C. by external cooling
2. 2
   여과filtered, saturated with sodium chloride
3. 3
   추출extracted with ether
4. 4
   추출The extract is extracted with half saturated sodium bicarbonate solutions
5. 5
   추출extracted with ether
6. 6
   세척The extract is washed with water and saturated sodium chloride solution
7. 7
   건조dried over magnesium sulfate
8. 8
   농축concentrated
9. 9
   기타The crude product is purified
10. 10
    기타by partition chromatography on Celite
11. 11
    기타to give an oil

실험 절차

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).

출처