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

HRID 715389Notes

Reaction equation

HRID 715389 reaction equation
[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>CC(N(C)C)=O>[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

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 DMA (54 mL) is stirred at rt for 4 hours. The reaction mixture is poured into water (100 mL) and extracted with n-hexane/EtOAc (1:10, 100 mL). The organic layer is washed with water (100 mL), and dried over sodium sulfate. After filtration, the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (5:1) to give 1.14 g (45% yield) of the title compound as colorless oil.

Workup

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

Sources & evidence

ORD record
ord-bf8c25c864af4104974e95365d7fd433
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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