反应详情

To a rapidly stirred mixture of 1-acetoxy-2-(6-carbethoxy-5,5-dimethylhexyl)cyclopent-1-ene (35 g., 0.113 mole) chloroform (95 ml.), water (125 ml.) and calcium carbonate (11.8 g.) cooled in an ice-bath is added dropwise over a period of thirty minutes a solution of bromine (18.8 g.) in carbon tetrachloride (31 ml.). After stirring in the cold for an additional 45 minutes the orange colored chloroform layer is separated and washed with dilute sodium bisulfite and saturated saline solution, dried over magnesium sulfate and taken to dryness in vacuo (bath temperature: 35°-40°) leaving an amber colored oil. A slurry of 100 ml. of N,N-dimethylacetamide and 16.5 g. of CaCO3 is stirred and heated to reflux under nitrogen flow. The above dried oil is added from a dropping funnel rapidly, maintaining reflux and nitrogen flow for 30 minutes. The cooled reaction mixture is filtered, and the precipitate is washed with ether. The filtrate is poured into two liters ice-cold water and is extracted with ether. The combined extracts and washing is washed with water, saturated saline, treated with decolorizing charcoal, filtered. The solvent evaporated in vacuo to give 24 g. (77%) of subject product.

1. temperaturecooled in an ice-bath
2. customis separated
3. washwashed with dilute sodium bisulfite and saturated saline solution
4. dry with materialdried over magnesium sulfate
5. customtaken to dryness in vacuo (bath temperature: 35°-40°)
6. customleaving an amber colored oil
7. temperatureheated
8. temperatureto reflux under nitrogen flow
9. customThe above dried oil
10. additionis added from a dropping funnel rapidly
11. temperaturemaintaining
12. temperaturereflux
13. customThe cooled reaction mixture
14. filtrationis filtered
15. washthe precipitate is washed with ether
16. additionThe filtrate is poured into two liters ice-cold water
17. extractionis extracted with ether
18. washThe combined extracts and washing
19. washis washed with water, saturated saline
20. additiontreated with decolorizing charcoal
21. filtrationfiltered
22. customThe solvent evaporated in vacuo
23. customto give 24 g