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

HRID 1869113

Reaktionsgleichung

Reaktionsgleichung von HRID 1869113
[CH3:1][N:2]([CH3:9])[CH2:3][CH2:4][O:5][CH2:6][CH2:7][OH:8].[Cl-].[CH2:11]([O:13][C:14](=[O:20])/[CH:15]=[CH:16]/[C:17](O)=[O:18])[CH3:12].C([O-])(O)=O.[Na+]>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[CH2:11]([O:13][C:14](=[O:20])[CH:15]=[CH:16][C:17]([O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][N:2]([CH3:9])[CH3:1])=[O:18])[CH3:12]

Komponenten

6

Edukt 3

HCID 743482-(2-(Dimethylamino)ethoxy)ethanolHCID 516892Sodium BicarbonateHCID 86609896Fumaric acid monoethylester monochloride

Produkt 1

HCID 86609895But-2-enedioic Acid 2-(2-dimethylamino-ethoxy)-ethyl Ester Ethyl EsterAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-93f5ca8be3ed455eadcb2d6a7259a55b
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638118B2

Verknüpfte Notizen

Wird geladen…