反应详情

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).

1. filtrationfiltered
2. additionThe filtrate is diluted with water, saturated with solid sodium chloride
3. extractionextracted with ether
4. washThe extract is washed with saturated sodium chloride solution
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated
7. customPartition chromatography of the residue on Celite
8. customgives white crystals, m.p. 58°-66° C., λmax