Potassium Carbonate → 3-Trifluoromethyl-6-(2-methylphenyl)-4,5,6,7-tetrahydrobenzofuran-4-one

HRID 1700475Notes

Reaction equation

HRID 1700475 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=[O:14])[CH2:11][C:10](=[O:15])[CH2:9]1.Br[CH2:17][C:18]([C:20]([F:23])([F:22])[F:21])=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:21][C:20]([F:23])([F:22])[C:18]1[C:11]2[C:12](=[O:14])[CH2:13][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])[CH2:9][C:10]=2[O:15][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 176065755-(2-Methylphenyl)cyclohexane-1,3-dione

Product 1

HCID 183174843-Trifluoromethyl-6-(2-methylphenyl)-4,5,6,7-tetrahydrobenzofuran-4-oneYield 8.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(2-methylphenyl)cyclohexane-1,3-dione (2.0 g), 1-bromo-3,3,3-trifluoroacetone (1.9 g), potassium carbonate (2.7 g) and dimethylformamide (30 ml) was stirred at room temperature for 2 hours, and then at 150° C. for 12 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added ethyl acetate. The mixture was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane). The resulting crystals were recrystallized from isopropylether and hexane to give colorless crystals of 3-trifluoromethyl-6-(2-methylphenyl)-4,5,6,7-tetrahydrobenzofuran-4-one (0.26 g).

Workup

  1. waitat 150° C. for 12 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. additionto the residue was added ethyl acetate
  4. washThe mixture was washed with water and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)
  8. customThe resulting crystals were recrystallized from isopropylether and hexane

Sources & evidence

ORD record
ord-c753b0ce6b8749cb88c2c9204cb37ba1
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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