Potassium Carbonate → HCID 21833755, compound

HRID 1741068Notes

Reaction equation

HRID 1741068 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][C:10](=O)[CH3:11])=[CH:4][C:3]=1[CH3:14].Cl.[NH2:16]O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:13][N:16]=[C:10]([CH3:11])[CH:9]=2)=[CH:4][C:3]=1[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 21833711HCID 21833711, compound

Product 1

HCID 21833755HCID 21833755, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(4-bromo-3-methylphenyl)butane-1,3-dione (D77) (615 mg; 0.0024 ml) in ethanol (15 ml) was treated with hydroxylamine hydrochloride (170 mg; 0.0024 mol) and potassium carbonate (336 mg; 0.0024 mol), and the mixture heated at reflux for 2.5 hours, then overnight at room temperature. The solvent was evaporated under reduced pressure and the residue partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and concentrated in vacuo to leave the crude isoxazole, which was purified by chromatography on silica gel, eluting with pentane, 60-80 petroleum-ether and ethyl acetate, to afford the title compound as a yellow crystalline material (477 mg, 78%).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2.5 hours
  3. customovernight
  4. customat room temperature
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue partitioned between water and ethyl acetate
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customto leave the crude isoxazole, which
  10. customwas purified by chromatography on silica gel
  11. washeluting with pentane, 60-80 petroleum-ether and ethyl acetate

Sources & evidence

ORD record
ord-b0f5f9c7670044a79c08f8b9efe952ed
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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