反应详情

A stirred mixture of 6.35 g. (20 mmoles) of 4-bromo-2-(carbethoxyhexyl)cyclopent-2-en-1-one (Example 9), 3.01 g. (11 moles) of silver carbonate, and 40 ml. of t-butanol is heated at 70° C. for 17 hours. The mixture is cooled and filtered. After evaporation of t-butanol the residue is treated with aqueous sodium chloride and extracted with 3:1 ether-hexane. The extract is washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The crude product is purified by chromatography on silica gel to give in order of elution: the subject compound as an oil; λmax.MeOH =219 mμ (8860); νmax.=1735 (ester carbonyl group), 1725 (ketone carbonyl group), and 1365 cm-1 (tert.-butyl group); and 4-hydroxy-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one also as an oil.

1. additionA stirred mixture of 6.35 g
2. temperatureThe mixture is cooled
3. filtrationfiltered
4. customAfter evaporation of t-butanol the residue
5. additionis treated with aqueous sodium chloride
6. extractionextracted with 3:1 ether-hexane
7. washThe extract is washed with saturated sodium chloride solution
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated
10. customThe crude product is purified by chromatography on silica gel
11. customto give in order of elution