Potassium Carbonate → 2-Methyl-2-(3-pyridin-3-yl-phenoxy)-propionic acid ethyl ester

HRID 1269489Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269489
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20]([O:22][C:23](=[O:28])[C:24](Br)([CH3:26])[CH3:25])[CH3:21]>CN(C)C=O.O>[CH2:20]([O:22][C:23](=[O:28])[C:24]([CH3:26])([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:3]=1)[CH3:25])[CH3:21]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 129379483-(Pyridin-3-yl)phenol

Produkt 1

HCID 688835012-Methyl-2-(3-pyridin-3-yl-phenoxy)-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-(3-hydroxyphenyl)pyridine (40.91 g, 0.239 mol) in 500 mL dimethylformamide was added potassium carbonate (148.62 g, 1.075 mol) and ethyl-2-bromoisobutyrate (157.8 mL, 1.075 mol). The mixture was heated to reflux under N2 with stirring for 18 h and cooled to ambient temperature. The resultant brown suspension was diluted with 1 L water and extracted with diethyl ether (3×500 mL). The organic phases were combined and dried over anhydrous sodium sulfate, filtered and concentrated to a volume of 1 L. The organic solution was diluted with 1 L water and made acidic with 6N HCl. The layers were separated and the organic phase extracted with 500 mL water. The acidic extractions were combined and made basic with 5N aqueous sodium hydroxide. This basic layer was extracted with diethyl ether (4×500 mL) and the extracts were combined, washed with 500 mL brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield crude 2-methyl-2-(3-pyridin-3-yl-phenoxy)-propionic acid ethyl ester as a pale yellow oil which was taken on to the next step without further purification.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux under N2
  3. extractionextracted with diethyl ether (3×500 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a volume of 1 L
  7. additionThe organic solution was diluted with 1 L water
  8. customThe layers were separated
  9. extractionthe organic phase extracted with 500 mL water
  10. extractionThe acidic extractions
  11. extractionThis basic layer was extracted with diethyl ether (4×500 mL)
  12. washwashed with 500 mL brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5961b57d3cf6431c8275ade16e93a9ba
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199243B2

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