Chloroacetone → HCID 18317544, compound

HRID 1700460Notes

Reaction equation

HRID 1700460 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][C:14](=[O:16])[CH2:13][C:12](=[O:17])[CH2:11]2)=[CH:6][CH:5]=1.Cl[CH2:19][C:20](=O)[CH3:21]>CN(C)C=O>[CH3:21][C:20]1[C:13]2[C:12](=[O:17])[CH2:11][CH:10]([C:7]3[CH:8]=[CH:9][C:4]([Br:3])=[CH:5][CH:6]=3)[CH2:15][C:14]=2[O:16][CH:19]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 183176135-(4-Bromophenyl)cyclohexane-1,3-dione

Product 1

HCID 18317544HCID 18317544, compoundYield 11.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide (10 ml) was suspended 60% sodium hydride (0.44 g, washed with hexane thrice), and to the suspension was added 5-(4-bromophenyl)cyclohexane-1,3-dione (2.6 g) and then was added chloroacetone (0.92 g), and the mixture was stirred at room temperature for 1 hour and then at 150° C. for 13 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution 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 hexane to give colorless crystals of 3-methyl-6-(4-bromophenyl)-4,5,6,7-tetrahydrobenzofuran-4-one (0.35 g).

Workup

  1. waitat 150° C. for 13 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution 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 hexane

Sources & evidence

ORD record
ord-8560ae19f5e24ec0ac248ce6530a7e8d
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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