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

HRID 1654119Notes

Reaction equation

HRID 1654119 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(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[F:12][C:11]([F:14])([F:13])[C:10]1[O:15][C:2]([CH3:16])=[CH:3][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 10933598Ethyl 4-oxo-2-(2,2,2-trifluoroacetyl)pentanoate

Product 1

HCID 2737208Ethyl 5-methyl-2-(trifluoromethyl)furan-3-carboxylateYield 60.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

24 g of the product of Stage A were mixed in 150 ml of toluene and 1.85 g of toluenesulfonic acid were added. The mixture was refluxed for 20 hours. The solvent was evaporated under reduced pressure at 40° C. The residue was chromatographed on silica (eluent: 95/5 hexane/ethyl acetate) to obtain 13.5 g of the expected product.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. customThe solvent was evaporated under reduced pressure at 40° C
  3. customThe residue was chromatographed on silica (eluent: 95/5 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4cfcf421f758470dac7cf27517bde940
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Reaction notes

Loading…