反应详情

9.8 g of 1,5-cyclooctanediol was dissolved in 150 ml of acetone, and to the solution was added Jones reagent prepared with 11.5 ml of sulfuric acid, 13 g of chromic acid and 20 ml of water. The solution was stirred at room temperature for fifteen minutes. To the reaction solution was added 2 ml of 2-propanol. Then, the solution was filtered through Celite. The residue was washed with dichloromethane and the washing solution was combined with the filtrate. The filtrate was washed with water and a saturated saline solution, and dried over anhydrous sodium sulfate. The solvent was evaporated, to afford a white solid. The crude product was dissolved in 200 ml of dimethylformamide. To the solution were added 6.6 g of imidazole and 12 g of tert-butylchlorodimethysilane. The reaction solution was stirred at room temperature overnight, and then cooled in an ice bath. To the resulting solution was added a saturated sodium bicarbonate aqueous solution. The reaction solution was extracted with diethylether, washed with a saturated saline solution, and dried over anhydrous sodium sulfate. The solvent was evaporated. The residue was subject to column chromatography on silica gel, and the eluate with ethyl acetate-hexane (1:9) was collected, to afford 13.6 g of the titled compound (a) as colorless liquid.

1. filtrationThen, the solution was filtered through Celite
2. washThe residue was washed with dichloromethane
3. washThe filtrate was washed with water
4. dry with materiala saturated saline solution, and dried over anhydrous sodium sulfate
5. customThe solvent was evaporated
6. customto afford a white solid
7. stirringThe reaction solution was stirred at room temperature overnight
8. temperaturecooled in an ice bath
9. extractionThe reaction solution was extracted with diethylether
10. washwashed with a saturated saline solution
11. dry with materialdried over anhydrous sodium sulfate
12. customThe solvent was evaporated
13. customthe eluate with ethyl acetate-hexane (1:9) was collected