Water → 3-(2-Ethoxyethoxy)-2-methylpyridine

HRID 1171776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1171776
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[C:9]([CH3:14])=[N:10][CH:11]=[CH:12][CH:13]=1.[CH2:15]([O:17][CH2:18][CH2:19]Cl)[CH3:16].O>CN(C=O)C.C(OCC)(=O)C>[CH2:15]([O:17][CH2:18][CH2:19][O:7][C:8]1[C:9]([CH3:14])=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:16]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 12341Ethane, 1-chloro-2-ethoxy-2×HCID 707192-Methylpyridin-3-ol

Produkt 1

HCID 670684753-(2-Ethoxyethoxy)-2-methylpyridineAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Potassium carbonate (2.20 g, 15.9 mmol) was added to a stirred solution of 3-hydroxy-2-methylpyridine (1.45 g, 13.3 mmol) and 2-chloroethyl ethyl ether (1.75 mL, 15.9 mmol) in DMF (7 mL) and the mixture was stirred at 70° C. overnight. The reaction was not complete and additional 2-chloroethyl ethyl ether (1 equiv.) and potassium carbonate (1 equiv.) were added and the mixture was stirred at 85° C. for 8 h. Water and ethyl acetate were added and the aqueous layer was extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated. The crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 50% ethyl acetate), obtaining 1.80 g (75%) the title compound.

Aufarbeitung

  1. stirringthe mixture was stirred at 85° C. for 8 h
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 50% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-cb5a5aa8113c4e34ae70efe5f2827f9c
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829707B2

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