2,4,6-Tris(1-methyl-3-trifluoromethylpyrazol-5-yloxy)pyridine → 2,6-Bis(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxypyridine

HRID 366299

Reaction equation

HRID 366299 reaction equation
C[O-].[K+].[CH3:4][N:5]1[C:9]([O:10][C:11]2[CH:16]=[C:15]([O:17][C:18]3N(C)N=C(C(F)(F)F)C=3)[CH:14]=[C:13]([O:28][C:29]3[N:33]([CH3:34])[N:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=3)[N:12]=2)=[CH:8][C:7]([C:39]([F:42])([F:41])[F:40])=[N:6]1>CO>[CH3:34][N:33]1[C:29]([O:28][C:13]2[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=[C:11]([O:10][C:9]3[N:5]([CH3:4])[N:6]=[C:7]([C:39]([F:40])([F:41])[F:42])[CH:8]=3)[N:12]=2)=[CH:30][C:31]([C:35]([F:38])([F:36])[F:37])=[N:32]1

Participants

4

Reactant 2

HCID 158696782,4,6-Tris(1-methyl-3-trifluoromethylpyrazol-5-yloxy)pyridineHCID 23664618Potassium methoxide

Product 1

HCID 225726302,6-Bis(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxypyridineYield 43.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 3 ml aliquot of a 25 % solution of potassium methylate (10 mmol) in dry methanol is added to a solution of 5.7 g (10 mmol) 2,4,6-tris-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)pyridine in 20 ml anhydrous methanol. After 2 hours at ambient temperature, the reaction mixture is heated to reflux. The solvent is removed under reduced pressure and ethyl acetate is added to the residue. The mixture is washed with a 2 N sodium hydroxide solution. After drying and filtration of the organic layer, the solvents are removed and the residue is washed with diisopropyl ether and pentane. Colorless crystals (1.9 g, 43 % yield) of melting point 107° C. are obtained.

Workup

  1. temperaturethe reaction mixture is heated to reflux
  2. customThe solvent is removed under reduced pressure and ethyl acetate
  3. additionis added to the residue
  4. washThe mixture is washed with a 2 N sodium hydroxide solution
  5. customAfter drying
  6. filtrationfiltration of the organic layer
  7. customthe solvents are removed
  8. washthe residue is washed with diisopropyl ether and pentane

Sources & evidence

ORD record
ord-6759362e203b434a933ffc01546fab73
Source dataset
uspto-grants-2000_10
Patent number
US06130188

Linked notes

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