2-(2-(Dimethylamino)ethoxy)ethanol → But-2-enedioic Acid 2-(2-dimethylamino-ethoxy)-ethyl Ester Ethyl Ester

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Reaction Steps

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.

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