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

HRID 2119944Notes

Reaction equation

HRID 2119944 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-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl-2,4-dioxovalerate in ethanol is added hydroxylamine hydrochloride and sodium hydrogen carbonate. The reaction mixture is then heated under reflux for 1 hour. After cooling, the mixture is evaporated to leave a clear liquid that was distilled to leave the title compound.

Workup

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

Sources & evidence

ORD record
ord-b38f7e11630e4136bdbf3c57897e38a1
Source dataset
uspto-grants-2004_02
Patent number
US06686352B2

Reaction notes

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