Water → Methyl 6-(2,2,2-trifluoroethoxy)picolinate

HRID 623428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 623428
[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[N:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][CH:6]=1.CI.[C:18](=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[F:15][C:2]([F:1])([F:14])[CH2:3][O:4][C:5]1[N:10]=[C:9]([C:11]([O:13][CH3:18])=[O:12])[CH:8]=[CH:7][CH:6]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 212530416-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acid

Produkt 1

HCID 67510684Methyl 6-(2,2,2-trifluoroethoxy)picolinateAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A mixture of 6-(2,2,2-trifluoroethoxy)picolinic acid (2.40 g, 10.9 mmol, Step-1), methyl iodide (3.39 mL, 54.3 mmol) and potassium carbonate (4.50 g, 32.6 mmol) in N,N-dimethylacetamide (54 mL) is stirred at room temperature for 4 hours. The reaction mixture is poured into water (100 mL) and extracted with n-hexane/ethyl acetate (1:10, 100 mL). The organic layer is washed with water (100 mL), dried over sodium sulfate, and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (5:1) to give 1.14 g (45% yield) of the title compound as colorless oil.

Aufarbeitung

  1. extractionextracted with n-hexane/ethyl acetate (1:10, 100 mL)
  2. washThe organic layer is washed with water (100 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-cda06d7b6082405999f359872291792b
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302991B2

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