Reaktion #95305

Reaktionsgleichung

KBr

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

acetone

water

→

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

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   workup.ADDITIONThe filtrate is diluted with water, saturated with solid sodium chloride
3. 3
   Extraktionextracted with ether
4. 4
   WaschenThe extract is washed with saturated sodium chloride solution
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Einengenconcentrated
7. 7
   SonstigePartition chromatography of the residue on Celite
8. 8
   Sonstigegives white crystals, m.p. 58°-66° C., λmax

Vorschrift

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).

Quelle