反应详情

To a stirred solution of 19.1 g. of crude 4-bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one (Example 8) in 310 ml. of ethylene glycol is added 15.6 g. (80 mmole) of silver fluoborate during 2 minutes. The exothermic reaction is controlled to give a temperature of 29° C., and after 1 minute the mixture is treated during 1 minute with 8.6 g. (λmmole) of 2,6-lutidine. The mixture is stirred at ambient temperature for 2 hours, diluted with water, and filtered. The filtrate is diluted with saturated sodium chloride solution and extracted with ether. The extract is washed with half-saturated sodium chloride solution containing a little hydrochloric acid and saturated sodium chloride solution. The extract is dried over magnesium sulfate and concentrated. Column chromatography of the residue on silica gel gives an oil, λmax.MeOH =216 mμ(8350); νmax.=3340 (hydroxyl groups), 1700 (carbonyl groups), and 1620 cm-1 (olefin group).

1. customThe exothermic reaction
2. customto give a temperature of 29° C.
3. additionafter 1 minute the mixture is treated during 1 minute with 8.6 g
4. filtrationfiltered
5. additionThe filtrate is diluted with saturated sodium chloride solution
6. extractionextracted with ether
7. washThe extract is washed with half-saturated sodium chloride solution
8. additioncontaining a little hydrochloric acid and saturated sodium chloride solution
9. dry with materialThe extract is dried over magnesium sulfate
10. concentrationconcentrated
11. customColumn chromatography of the residue on silica gel gives an oil, λmax