Réaction #95305

Équation de réaction

KBr

4-bromo-2-(8-carboxyoctyl)cyclopent-2-en-1-one

acetone

water

→

4-hydroxy-2-(8-carboxyoctyl)cyclopent-2-en-1-one

Solvants

MeOH

Conditions de réaction

Traitement

1. 1
   Filtrationfiltered
2. 2
   workup.ADDITIONThe filtrate is diluted with water, saturated with solid sodium chloride
3. 3
   Extractionextracted with ether
4. 4
   LavageThe extract is washed with saturated sodium chloride solution
5. 5
   Séchagedried over magnesium sulfate
6. 6
   Concentrationconcentrated
7. 7
   AutrePartition chromatography of the residue on Celite
8. 8
   Autregives white crystals, m.p. 58°-66° C., λmax

Mode opératoire

To a stirred solution of 57.2 g. of crude 4-bromo-2-(8-carboxyoctyl)cyclopent-2-en-1-one (Example 1280) in 500 ml. of acetone and 325 ml. of water at 3° C. is added 44.1 g. (0.226 moles) of silver fluoborate during a 15 minute period. The mixture is stirred at 0°-3° C. for 2 hours and filtered. The filtrate is diluted with water, saturated with solid sodium chloride, and extracted with ether. The extract is washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. Partition chromatography of the residue on Celite gives white crystals, m.p. 58°-66° C., λmax.MeOH =223 mμ (7800); νmax (KBr)=3340 (hydroxyl groups), 1705 (carbonyl groups), and 1625 cm-1 (olefin group).

Source