反应详情

温度

90 °C

p-Tolualdehyde (53 mL, 0.486 mol) was stirred in a solvent of chloroform (900 mL), slowly added with aminoacetaldehyde dimethyl acetal (59.3 mL, 0.486 mol), and stirred at 90° C. until about a half of the reaction solution had evaporated. The reaction solution was cooled to room temperature, and the yellow reaction solution was dissolved in chloroform (400 mL), followed by cooling to 0° C. or lower. The reaction solution was slowly added with ethyl chloroformate (48 mL, 0.486 mol) and triethyl phosphite (104 mL, 0.583 mol), followed by stirring for 24 hours at room temperature. The reaction solution was cooled to 0° C. or lower, slowly added with titanium tetrachloride (213.6 mL, 1.94 mol), and refluxed for 12 hours or more. The temperature of the reaction solution was adjusted to room temperature and stirred for over 12 hours. The reaction mixture was poured over an ice water to separate the organic layer and the aqueous layer, and the aqueous layer was washed with dichloromethane. The aqueous layer was poured into a saturated potassium sodium tartrate solution, and adjusted to have a pH value of 9 by adding an aqueous ammonia solution, and then extracted with dichloromethane. The combined organic layer thus obtained was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound (46.3 g, 66%).

1. customhad evaporated
2. temperatureThe reaction solution was cooled to room temperature
3. dissolutionthe yellow reaction solution was dissolved in chloroform (400 mL)
4. temperatureby cooling to 0° C.
5. stirringby stirring for 24 hours at room temperature
6. temperatureThe reaction solution was cooled to 0° C.
7. temperaturerefluxed for 12 hours or more
8. customwas adjusted to room temperature
9. stirringstirred for over 12 hours
10. customto separate the organic layer
11. washthe aqueous layer, and the aqueous layer was washed with dichloromethane
12. additionThe aqueous layer was poured into a saturated potassium sodium tartrate solution
13. additionby adding an aqueous ammonia solution
14. extractionextracted with dichloromethane
15. customThe combined organic layer thus obtained
16. dry with materialwas dried over anhydrous sodium sulfate
17. concentrationconcentrated under reduced pressure