Chloroacetone → 6-(4-Fluorophenyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-one

HRID 1700459Notes

Reaction equation

HRID 1700459 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[CH2:11][C:10](=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[O-]CC.[Na+].Cl[CH2:21][C:22](=O)[CH3:23]>C(O)C.CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[C:11]3[C:22]([CH3:23])=[CH:21][O:15][C:10]=3[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 7301365-(4-Fluorophenyl)cyclohexane-1,3-dioneHCID 2723922Sodium ethoxide

Product 1

HCID 183176736-(4-Fluorophenyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(4-fluorophenyl)cyclohexane-1,3-dione (mp175-176° C.; 1.03 g) in ethanol (10 ml) was added sodium ethoxide (0.37 g), and the mixture was stirred, under argon atmosphere, at room temperature for 15 minutes. To the mixture was added a solution of chloroacetone (0.45 ml) in DMF (10 ml), and the mixture was stirred at 100° C. overnight (13 hours). The reaction solution was cooled and concentrated under reduced pressure. To the residue was added ice-water, and the mixture was extracted with ethyl acetate. The upper layer was washed with saturated brine, dried (anhydrous magnesium sulfate), and concentrated under reduced pressure, and the residue was subjected to silica gel chromatography and eluted with ethyl acetate/hexane to give 6-(4-fluorophenyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-one (0.12 g).

Workup

  1. stirringthe mixture was stirred at 100° C. overnight (13 hours)
  2. temperatureThe reaction solution was cooled
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added ice-water
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe upper layer was washed with saturated brine
  7. dry with materialdried (anhydrous magnesium sulfate)
  8. concentrationconcentrated under reduced pressure
  9. washeluted with ethyl acetate/hexane

Sources & evidence

ORD record
ord-3fa7a6ebb5f54014a74a271eb56030ba
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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