تفاعل #95256

معادلة التفاعل

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

المذيبات

MeOH

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe temperature is maintained at 25°-30° C. by external cooling
2. 2
   ترشيحfiltered, saturated with sodium chloride
3. 3
   استخلاصextracted with ether
4. 4
   استخلاصThe extract is extracted with half saturated sodium bicarbonate solutions
5. 5
   استخلاصextracted with ether
6. 6
   غسيلThe extract is washed with water and saturated sodium chloride solution
7. 7
   تجفيفdried over magnesium sulfate
8. 8
   تركيزconcentrated
9. 9
   أخرىThe crude product is purified
10. 10
    أخرىby partition chromatography on Celite
11. 11
    أخرىto give an oil

الإجراء التجريبي

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).

المصدر