Acetic Acid → HCID 13792860, compound

HRID 2257044Notes

Reaction equation

HRID 2257044 reaction equation
[C:1]([CH:4]([C:11](=[O:13])[CH3:12])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)[CH3:2].Cl.[NH2:15]O.CC([O-])=O.[Na+].C(O)(=O)C>C(O)C>[CH3:2][C:1]1[C:4]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:11]([CH3:12])[O:13][N:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 87820Ethyl 3-acetyl-4-oxopentanoateHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 13792860HCID 13792860, compoundYield 3.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-acetyl-4-oxopentanoate (37.24 g, 0.2 mol), hydroxylamine hydrochloride (14.6 g, 0.21 mol), NaOAc (17.23 g, 0.21 mol) and ethanol (500 mL) was refluxed for 4 hours. The reaction mixture was filtered, the filtrate was concentrated in vacuo and the residue was heated in acetic acid (12.61 g, 0.21 mol) and toluene (300 mL) for 6 to 6.5 hours with the removal of water. The reaction mixture was filtered and the filtrate was concentrated in vacuo to afford a tan oil which crystallized on cooling. The product was collected by filtration and washed with ether to afford 1.26 g of ethyl 3,5-dimethyl-4-isoxazolylacetate, m.p. 180°-182° C. Additional product was obtained by concentration of the ether filtrate and distillation of the residue at 69°-81.5° C. and 0.05 mm Hg to afford a total of 31.18 g (85%).

Workup

  1. temperaturewas refluxed for 4 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customtoluene (300 mL) for 6 to 6.5 hours with the removal of water
  5. filtrationThe reaction mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customto afford a tan oil which
  8. customcrystallized
  9. temperatureon cooling
  10. filtrationThe product was collected by filtration
  11. washwashed with ether

Sources & evidence

ORD record
ord-6cd3bddd12714759b9b3a2bd2fee0b6f
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

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