Ammonium Acetate → 5-Acetyl-2,4-dimethyloxazole

HRID 1985740Notes

Reaction equation

HRID 1985740 reaction equation
Cl[CH2:2][C:3]([CH2:5][C:6](=O)[CH3:7])=[O:4].[C:9]([O-:12])(=O)[CH3:10].[NH4+:13]>C(O)(=O)C>[CH3:10][C:9]1[O:12][C:5]([C:3](=[O:4])[CH3:2])=[C:6]([CH3:7])[N:13]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 144968561-Chloro-2,4-pentanedione

Product 1

HCID 3184185-Acetyl-2,4-dimethyloxazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Chloroacetylacetone 8 g (59.4 mmol) is dissolved in 70 ml of glacial acetic acid and ammonium acetate 13.7 g (178.2 mmol) is then added and the mixture is refluxed for 4 hours. The solution is cooled, brought to pH 5 and extracted into ether; the organic layer is dried over Na2SO4 and concentrated to dryness in vacuo. The residue is purified by column chromatography on silica gel using 8:2 hexane:ethyl acetate as eluent. The 2,4-dimethyl-5-acetyloxazole is obtained as orange needles (2.2 g, 27%).

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. temperatureThe solution is cooled
  3. extractionextracted into ether
  4. dry with materialthe organic layer is dried over Na2SO4
  5. concentrationconcentrated to dryness in vacuo
  6. customThe residue is purified by column chromatography on silica gel using 8:2 hexane

Sources & evidence

ORD record
ord-68c124f39a5749b6b4c6427b391caacf
Source dataset
uspto-grants-2009_06
Patent number
US07547709B2

Reaction notes

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