반응 #349092

반응 방정식

KBr

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

acetone

water

→

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

용매

MeOH

반응 조건

후처리

1. 1
   여과filtered
2. 2
   workup.ADDITIONThe filtrate is diluted with water, saturated with solid sodium chloride
3. 3
   추출extracted with ether
4. 4
   세척The extract is washed with saturated sodium chloride solution
5. 5
   건조dried over magnesium sulfate
6. 6
   농축concentrated
7. 7
   기타Partition chromatography of the residue on Celite
8. 8
   기타gives white crystals, m.p. 58°-66° C., λmax

실험 절차

To a stirred solution of 57.2 g. of crude 4-bromo-2-(8-carboxyoctyl)cyclopent-2-en-1-one (Example 13) 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 1625-1 (olefin group).

출처