2-Methoxyethanol → 3-(2-Methoxyethoxy)pyridine-2-carboxylic acid

HRID 341563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 341563
F[C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:11][O:12][CH2:13][CH2:14][OH:15].CC(C)([O-])C.[K+]>O.Cl>[CH3:11][O:12][CH2:13][CH2:14][O:15][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 80192-MethoxyethanolHCID 27627863-Fluoropyridine-2-carboxylic acidHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 613800493-(2-Methoxyethoxy)pyridine-2-carboxylic acidAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

3-Fluoropyridine-2-carboxylic acid (150 mg, 1.06 mol), 2-methoxyethanol (1.5 mL) and potassium tert-butoxide (356 mg, 3.18 mmol) were charged to a sealed tube under nitrogen then stirred at 100 C for 18 h. The mixture was then diluted with water (3 mL), 1M HCl was added to bring the solution to pH 5 and the mixture was extracted with DCM (2×5 mL). 1M HCl was added to the aqueous layer to bring the solution to pH 3 and the mixture was extracted with DCM (2×5 mL). The combined organic extractions were dried over sodium sulfate and evaporated under vacuum to afford the title compound as a brown gum (54 mg, 26%). Method C HPLC-MS: MH+ requires m/z=198. Found: m/z=198, Rt=0.29 min.

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture was extracted with DCM (2×5 mL)
  3. addition1M HCl was added to the aqueous layer
  4. extractionthe mixture was extracted with DCM (2×5 mL)
  5. extractionThe combined organic extractions
  6. dry with materialwere dried over sodium sulfate
  7. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-537e81a8fa4444af97e96aaebc735492
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895733B2

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