Chloroacetone → 3-Methyl-6-(2-thienyl)-4,5,6,7-tetrahydrobenzofuran-4-one

HRID 1700473Notes

Reaction equation

HRID 1700473 reaction equation
[H-].[Na+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH:8]1[CH2:13][C:12](=[O:14])[CH2:11][C:10](=[O:15])[CH2:9]1.Cl[CH2:17][C:18](=O)[CH3:19]>CN(C)C=O>[CH3:19][C:18]1[C:11]2[C:10](=[O:15])[CH2:9][CH:8]([C:4]3[S:3][CH:7]=[CH:6][CH:5]=3)[CH2:13][C:12]=2[O:14][CH:17]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 5736855-(2-Thienyl)cyclohexane-1,3-dione

Product 1

HCID 183173293-Methyl-6-(2-thienyl)-4,5,6,7-tetrahydrobenzofuran-4-oneYield 15%

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-(2-thienyl)cyclohexane-1,3-dione (1.9 g) and then was added chloroacetone (0.92 g). 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-(2-thienyl)-4,5,6,7-tetrahydrobenzofuran-4-one (0.34 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-12a371b764bf4e9abfe4e95b9b875463
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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