反应详情

To the solution of 2-[2-(dimethylamino)-ethoxy]ethanol (13.35 g, 100 mmol, 1.9 equiv.) and 4-dimethylaminopyridine (50 mg) in toluene (80 ml) is added a solution of fumaric acid monoethylester monochloride (8.50 g, 52 mmol, 1.0 equiv.) in toluene (20 ml) at 23° C. over 25 min. The temperature rises to 34° C. and an orange suspension is formed. After 5 h stirring at room temperature, the mixture is poured on ice-cooled saturated aqueous NaHCO3 solution and the product is extracted with ethyl acetate. The organic layer is washed 3 times with H2O, then twice with brine. It is then dried over MgSO4 and concentrated in a rotary evaporator. The residue is dissolved in methyl t-butyl ether and SiO2 (6.0 g) is added to the solution. The suspension is shaken vigorously, then filtered and again concentrated and dried under high vacuum (23° C., 0.05 mbar). This yields the product (6.71 g, 50%) as a yellow liquid.

1. customrises to 34° C.
2. customan orange suspension is formed
3. additionthe mixture is poured on ice-
4. extractionthe product is extracted with ethyl acetate
5. washThe organic layer is washed 3 times with H2O
6. dry with materialIt is then dried over MgSO4
7. concentrationconcentrated in a rotary evaporator
8. dissolutionThe residue is dissolved in methyl t-butyl ether
9. additionSiO2 (6.0 g) is added to the solution
10. stirringThe suspension is shaken vigorously
11. filtrationfiltered
12. concentrationagain concentrated
13. customdried under high vacuum (23° C., 0.05 mbar)