Water → 2,6-Dimethyl-3-(2,2,2-trifluoroethoxy)pyridine

HRID 511826

Reaction equation

HRID 511826 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:22][C:23]([F:26])([F:25])[F:24])(=O)=O.O>CN(C=O)C>[CH3:1][C:2]1[C:7]([O:8][CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 707322,6-Dimethyl-3-pyridinolHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

Product 1

HCID 672902682,6-Dimethyl-3-(2,2,2-trifluoroethoxy)pyridineYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2,6-dimethylpyridin-3-ol (5.0 g, 41 mmol) and cesium carbonate (15 g, 47 mmol) in DMF (50 mL) was added 2,2,2-trifluoroethyl trifluoromethane-sulfonate (11 mL, 47 mmol) dropwise. The reaction mixture was stirred at room temperature for 1 hour. After being stirred at room temperature for 18 hours, the mixture was poured into H2O, and the aqueous phase was extracted with ethyl acetate (twice). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to give 8.3 g (quantitative yield) of the title compound as a brown oil:

Workup

  1. stirringAfter being stirred at room temperature for 18 hours
  2. extractionthe aqueous phase was extracted with ethyl acetate (twice)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-772556a1c68b411b84ff083a4711911e
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Linked notes

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