Chloroacetone → HCID 18317605, compound

HRID 1700457Notes

Reaction equation

HRID 1700457 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][C:12](=[O:14])[CH2:11][C:10](=[O:15])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C[O-].[Na+].Cl[CH2:20][C:21](=O)[CH3:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:9][C:10](=[O:15])[C:11]3[C:21]([CH3:22])=[CH:20][O:14][C:12]=3[CH2:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 102649515-(3-bromophenyl)cyclohexane-1,3-dioneHCID 10942334Sodium Methoxide

Product 1

HCID 18317605HCID 18317605, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(3-bromophenyl)cyclohexane-1,3-dione (mp182-183° C.; 1.34 g) in DMF (20 ml) was added sodium methoxide (0.30 g), and the mixture was stirred, under argon atmosphere, at room temperature for 15 minutes. To the mixture was added chloroacetone (0.45 ml), and the mixture was stirred at 90° C. for 2 hours. To the mixture was added potassium carbonate (0.69 g), and the mixture was stirred at 150° C. overnight (13 hours). The reaction solution was cooled, to which was added ice-water. The mixture was extracted with ethyl acetate, and the upper layer was washed with saturated brine, dried (anhydrous magnesium sulfate), and concentrated under reduced pressure. The residue was subjected to silica gel chromatography and eluted with ethyl acetate/hexane to give 6-(3-bromophenyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-one (0.14 g).

Workup

  1. stirringthe mixture was stirred at 90° C. for 2 hours
  2. stirringthe mixture was stirred at 150° C. overnight (13 hours)
  3. temperatureThe reaction solution was cooled, to which
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe upper layer was washed with saturated brine
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. concentrationconcentrated under reduced pressure
  8. washeluted with ethyl acetate/hexane

Sources & evidence

ORD record
ord-29d00d0d28ab4041824f89e21960be4a
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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