Chloroacetone → HCID 10858234, compound

HRID 1700467Notes

Reaction equation

HRID 1700467 reaction equation
[Cl: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.[H-].[Na+].Cl[CH2:19][C:20](=O)[CH3:21]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=[O:14])[C:11]2[C:20]([CH3:21])=[CH:19][O:15][C:10]=2[CH2:9]1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 8753605-(2-Chlorophenyl)cyclohexane-1,3-dione

Product 1

HCID 10858234HCID 10858234, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(2-chlorophenyl)cyclohexane-1,3-dione (mp157-158° C.; 1.11 g) in DMF (20 ml) was added 60% sodium hydride (0.22 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 150° C. overnight (15 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-(2-chlorophenyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-one (0.35 g).

Workup

  1. stirringthe mixture was stirred at 150° C. overnight (15 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-276facb8fdd84e8284f1286a349a0b90
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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