Ethyl pyruvate → Ethyl (2E)-2-(hydroxyimino)propanoate

HRID 2299706Notes

Reaction equation

HRID 2299706 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([CH3:4])=O.Cl.[NH2:10][OH:11].C([O-])(=O)C.[Na+]>C(O)C>[OH:11]/[N:10]=[C:2](\[CH3:4])/[C:1]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 12041Ethyl pyruvateHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 9614318Ethyl (2E)-2-(hydroxyimino)propanoateYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl pyruvate (9.50 g), hydroxylamine hydrochloride (6.82 g), sodium acetate (10.1 g) and ethanol (150 ml) was heated under reflux for 17 hours. The reaction mixture was concentrated, and the residue was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and then concentrated. The residual crystals were recrystallized from ethyl acetate-hexane to obtain ethyl E-2-hydroxyiminopropionate (6.33 g, yield 59%) as colorless crystals. m.p. 98-99° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 17 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionthe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residual crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d0676063145d4f109d3710453fd474dc
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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