Réaction #95256

Équation de réaction

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

Solvants

MeOH

Conditions de réaction

Traitement

1. 1
   TempératureThe temperature is maintained at 25°-30° C. by external cooling
2. 2
   Filtrationfiltered, saturated with sodium chloride
3. 3
   Extractionextracted with ether
4. 4
   ExtractionThe extract is extracted with half saturated sodium bicarbonate solutions
5. 5
   Extractionextracted with ether
6. 6
   LavageThe extract is washed with water and saturated sodium chloride solution
7. 7
   Séchagedried over magnesium sulfate
8. 8
   Concentrationconcentrated
9. 9
   AutreThe crude product is purified
10. 10
    Autreby partition chromatography on Celite
11. 11
    Autreto give an oil

Mode opératoire

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).

Source