反应详情

8N Jones' reagent (0.4 ml.) was added to a stirred solution of 2-(7-hydroxyheptyl)-3-(4-ethyl-3-oxo-1-octenyl)cyclopentanol (0.42 g.) in acetone (4 ml.) at below 20°C. at such a rate that the deep red coloration caused by the addition of one drop of reagent had changed to green before addition of the next drop. The reaction mixture was diluted with sufficient water to dissolve the precipitated chromium salts and then extracted three times with diethyl ether. The combined ether extracts were washed with 2N aqueous sulphuric acid and then added to 10% aqueous sodium carbonate (50 ml.) and stirred for 1 hour. The aqueous layer was separated and covered with a layer of diethyl ether and concentrated hydrochloric acid added dropwise until the pH was 1. The ether layer was separated and the aqueous layer again extracted with diethyl ether. The combined extracts were dried over magnesium sulphate and the ether was removed in vacuo to give 7-[2-oxo-5-(4-ethyl-3-oxo- 1-octenyl)cyclopentyl]-heptanoic acid (0.12 g.), νmax 1620 cm-1, 1680 cm-1, 1700 cm-1 and 1730 cm-1 (liquid film).

1. additiongreen before addition of the next drop
2. extractionextracted three times with diethyl ether
3. washThe combined ether extracts were washed with 2N aqueous sulphuric acid
4. additionadded to 10% aqueous sodium carbonate (50 ml.)
5. customThe aqueous layer was separated
6. additionadded dropwise until the pH was 1
7. customThe ether layer was separated
8. extractionthe aqueous layer again extracted with diethyl ether
9. dry with materialThe combined extracts were dried over magnesium sulphate
10. customthe ether was removed in vacuo