Water → Pyridine, 2-methoxy-4-(trifluoromethyl)-

HRID 1912265Notes

Reaction equation

HRID 1912265 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.[CH3:12][O-:13].[Na+].O>CO>[F:9][C:8]([F:11])([F:10])[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([O:13][CH3:12])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1449582-Chloro-4-(trifluoromethyl)pyridineHCID 10942334Sodium Methoxide

Product 1

HCID 18539797Pyridine, 2-methoxy-4-(trifluoromethyl)-Yield 85.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution having 5.05 g (27.8 mmol) of 2-chloro-4-trifluoromethylpyridine and 3.59 g (66.5 mmol) of sodium methoxide dissolved in 40 ml of methanol was stirred under reflux with heating for 4 hours. Water was added to terminate the reaction, followed by extraction with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and subjected to filtration on the pad of a silica gel cake. The solvent was distilled off under reduced pressure to obtain 4.19 g (yield: 85%) of 4-trifluoromethyl-2-methoxypyridine.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 4 hours
  3. customto terminate
  4. customthe reaction
  5. extractionfollowed by extraction with diethyl ether
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationsubjected to filtration on the pad of a silica gel cake
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ef417b3050c7492ba7de4fbd179ff0db
Source dataset
uspto-grants-2013_12
Patent number
US08609150B2

Reaction notes

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