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

HRID 536090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 536090
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-03fed8b67ae14aaebbaee8f5a82c3451
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859568B2

Notizen zur Reaktion

Wird geladen…