p-Toluenesulfonic acid → Ethyl 5-methyl-2-(trifluoromethyl)furan-3-carboxylate

HRID 1610325Notes

Reaction equation

HRID 1610325 reaction equation
O=[C:2]([CH3:16])[CH2:3][CH:4]([C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:16][C:2]1[O:15][C:10]([C:11]([F:14])([F:13])[F:12])=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 10933598Ethyl 4-oxo-2-(2,2,2-trifluoroacetyl)pentanoate

Product 1

HCID 2737208Ethyl 5-methyl-2-(trifluoromethyl)furan-3-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 4-oxo-2-(2,2,2-trifluoroacetyl)valerate (40 g, 167 mmol) in toluene (250 ml) was added p-toluenesulfonic acid (3 g, 16 mmol) and the mixture was heated under reflux overnight in a Dean-Stark apparatus under dehydrated conditions. The reaction solution was concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give ethyl 5-methyl-2-(trifluoromethyl)-3-furancarboxylate (25.8 g, 70%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight in a Dean-Stark apparatus under dehydrated conditions
  3. concentrationThe reaction solution was concentrated
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-93cfbafd18084f429ba2fcb6e0fd0505
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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