Ethyl 2,4-dioxovalerate → Ethyl 5-methylisoxazole-3-carboxylate

HRID 2119979Notes

Reaction equation

HRID 2119979 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[C:5](=O)[CH2:6][C:7](=[O:9])[CH3:8])[CH3:2].Cl.[NH2:13]O.C(=O)([O-])O.[Na+]>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]([CH3:8])[O:9][N:13]=1)=[O:11])[CH3:2]

Participants

5

Reactant 3

HCID 69208Ethyl 2,4-dioxovalerateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 76677Ethyl 5-methylisoxazole-3-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl-2,4-dioxovalerate (20 g, 126 mmol) in ethanol (85 mL), was added hydroxylamine hydrochloride (8.8 g, 126 mmol) and sodium hydrogen carbonate (10.6 g, 0.126 mmol). The reaction mixture was then heated under reflux for 1 hour. After cooling, the mixture was evaporated to leave a clear liquid that was distilled to leave the title compound as a colorless liquid (13.3 g, 68%); m/z (EI) 156.0 (MH).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. customthe mixture was evaporated
  5. customto leave a clear liquid that
  6. distillationwas distilled

Sources & evidence

ORD record
ord-5ce2f9395f8c4145a67d19d5f43e81f6
Source dataset
uspto-grants-2004_02
Patent number
US06686352B2

Reaction notes

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