Dimethylformamide → 2-(3,4-Dichlorophenoxy)-3-(dimethylamino)prop-2-enal

HRID 1831048

Reaktionsgleichung

Reaktionsgleichung von HRID 1831048
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]([CH3:10])[CH:8]=O.C([O:13][CH:14](OCC)[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)C.C(=O)([O-])[O-].[K+].[K+]>O.C(Cl)(Cl)Cl>[Cl:24][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[Cl:23])[O:16][C:15](=[CH:8][N:7]([CH3:10])[CH3:6])[CH:14]=[O:13]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 27820221,2-Dichloro-4-(2,2-diethoxyethoxy)benzene

Produkt 1

HCID 545558182-(3,4-Dichlorophenoxy)-3-(dimethylamino)prop-2-enalAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Phosphorus oxychloride (18.4 g, 120 mmol) was added to dimethylformamide (8.8 g, 120 mmol), maintaining the temperature below 25° C. by an external ice-bath. Upon completion of the addition the reaction mixture was heated to 50° C. for 45 minutes and then cooled to room temperature. Chloroform (35 ml) was added and the resulting solution was brought to reflux. 3,4-Dichlorophenoxyacetaldehyde diethylacetal (9.61 g, 40.0 mmol) was added in portions. After heating for 3 hours at reflux the solution was cooled to room temperature and poured carefully onto a solution of potassium carbonate (115 g) in water (100 ml). The mixture was cooled in an ice-bath to around room temperature and extracted twice with dichloromethane. The combined organic layers were dried over sodium sulphate, filtered and evaporated in vacuo yielding a brown oil, which was purified by flash column chromatography (SiO2, ethyl acetate) yielding the title compound (5.38 g, 52% yield) as a brown solid.

Aufarbeitung

  1. temperaturemaintaining the temperature below 25° C. by an external ice-bath
  2. additionUpon completion of the addition the reaction mixture
  3. temperaturecooled to room temperature
  4. temperatureto reflux
  5. temperatureAfter heating for 3 hours
  6. temperatureat reflux the solution
  7. temperaturewas cooled to room temperature
  8. temperatureThe mixture was cooled in an ice-bath to around room temperature
  9. extractionextracted twice with dichloromethane
  10. dry with materialThe combined organic layers were dried over sodium sulphate
  11. filtrationfiltered
  12. customevaporated in vacuo
  13. customyielding a brown oil, which
  14. customwas purified by flash column chromatography (SiO2, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-448f71b415b94259a3968286aa6b65fb
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067517B2

Verknüpfte Notizen

Wird geladen…