Reacción #95256

Ecuación de reacción

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

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe temperature is maintained at 25°-30° C. by external cooling
2. 2
   Filtraciónfiltered, saturated with sodium chloride
3. 3
   Extracciónextracted with ether
4. 4
   ExtracciónThe extract is extracted with half saturated sodium bicarbonate solutions
5. 5
   Extracciónextracted with ether
6. 6
   LavadoThe extract is washed with water and saturated sodium chloride solution
7. 7
   Secadodried over magnesium sulfate
8. 8
   Concentraciónconcentrated
9. 9
   OtroThe crude product is purified
10. 10
    Otroby partition chromatography on Celite
11. 11
    Otroto give an oil

Procedimiento

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).

Fuente