反应详情

To tetrahydrofuran (100 mL), oily sodium hydride (purity 60% by weight, 18 g, 450 mmol) was added and 2-(dimethylamino)ethanol (16.1 g, 180 mmol) was added dropwise at 0° C., and then the mixture was refluxed for 3 hours. To this suspension, toluene (80 mL) and tetrahydrofuran (25 mL) were added. A toluene (200 mL)/tetrahydrofuran (25 mL) mixed solution of p-toluenesulfonyl chloride (37.2 g, 195 mmol) was added dropwise at 0 to 5° C., followed by stirring at the same temperature for 1 hour. After further stirring for 1 hour under heating at reflux, the mixture was left standing to cool to room temperature. After adding dropwise 2-(dimethylamino)cyclohexanol (21.5 g, 150 mmol) at room temperature, potassium iodide (29.9 g, 180 mmol) was added. After stirring for 9 hours under heating at reflux, the reaction solution was left standing to cool to room temperature. Water was added and the solution was extracted with ethyl acetate, and then the organic phase was washed with water and saturated saline. This organic phase was dried over an anhydrous magnesium sulfate powder and then concentrated under reduced pressure. The residue was distilled under reduced pressure to obtain 2.3 g (in a yield of 7%) of the objective compound as a yellow liquid.

1. temperaturethe mixture was refluxed for 3 hours
2. additionwas added dropwise at 0 to 5° C.
3. stirringAfter further stirring for 1 hour
4. temperatureunder heating
5. temperatureat reflux
6. waitthe mixture was left
7. stirringAfter stirring for 9 hours
8. temperatureunder heating
9. temperatureat reflux
10. waitthe reaction solution was left
11. temperatureto cool to room temperature
12. extractionthe solution was extracted with ethyl acetate
13. washthe organic phase was washed with water and saturated saline
14. dry with materialThis organic phase was dried over an anhydrous magnesium sulfate powder
15. concentrationconcentrated under reduced pressure
16. distillationThe residue was distilled under reduced pressure