5-Methyl-2-(trifluoromethyl)-3-furancarboxylic acid → 2-Methyl-5-(trifluoromethyl)furan

HRID 1610327Notes

Reaction equation

HRID 1610327 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]([F:10])([F:9])[F:8])=[C:4](C(O)=O)[CH:3]=1>N1C2C(=CC=CC=2)C=CC=1.S([O-])([O-])(=O)=O.[Cu+].[Cu+]>[CH3:1][C:2]1[O:6][C:5]([C:7]([F:10])([F:9])[F:8])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 27821835-Methyl-2-(trifluoromethyl)-3-furancarboxylic acid

Product 1

HCID 109536882-Methyl-5-(trifluoromethyl)furanYield 54%

Reagents, catalysts & solvents 2

HCID 134737Sulfuric acid, copper(1+) salt (1:2)CatalystHCID 7047QuinolineSolvent

Procedure

To a solution of 5-methyl-2-(trifluoromethyl)-3-furancarboxylic acid (20 g, 103 mmol) in quinoline (36 ml) was added copper (I) sulfate (1 g, 6.3 mmol). While bubbling nitrogen, the mixture was immersed in an oil bath at 230° C. until gas generation ceased. The generated gas was collected and distilled again to give 2-methyl-5-(trifluoromethyl)furan (8.34 g, 54%).

Workup

  1. customWhile bubbling nitrogen
  2. customthe mixture was immersed in an oil bath at 230° C. until gas generation
  3. customThe generated gas was collected
  4. distillationdistilled again

Sources & evidence

ORD record
ord-1ad3a181e7444430b968eb54d685f291
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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