反応 #95305

反応方程式

KBr

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

acetone

water

→

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

溶媒

MeOH

反応条件

後処理

1. 1
   ろ過filtered
2. 2
   workup.ADDITIONThe filtrate is diluted with water, saturated with solid sodium chloride
3. 3
   抽出extracted with ether
4. 4
   洗浄The extract is washed with saturated sodium chloride solution
5. 5
   乾燥dried over magnesium sulfate
6. 6
   濃縮concentrated
7. 7
   その他Partition chromatography of the residue on Celite
8. 8
   その他gives white crystals, m.p. 58°-66° C., λmax

実験手順

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).

出典