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

HRID 243774Notes

Reaction equation

HRID 243774 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-fdb216d1c529489cbb2ed0210183f5ba
Source dataset
uspto-grants-2014_02
Patent number
US08653277B2

Reaction notes

Loading…