Acetic Acid → HCID 58664156, compound

HRID 1182820Notes

Reaction equation

HRID 1182820 reaction equation
[C:1]([OH:4])(=O)[CH3:2].O=C(C)C([C:9]1[CH:13]=[CH:12][O:11][C:10]=1[C:14](O)=O)C.[C:18]([O-])(=O)[CH3:19].[NH4+:22]>O>[O:11]1[CH:12]=[CH:13][CH:9]=[C:10]1[C:14]1[O:4][C:1]([CH3:2])=[C:18]([CH3:19])[N:22]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 66706166HCID 66706166, compound

Product 1

HCID 58664156HCID 58664156, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The acetic acid (180 mL) solution of 3-oxobutan-2-yl furan-2-carboxylic acid (18.2 g, 100 mmol) and ammonium acetate (38.6 g, 500 mmol) was stirred for 5 hrs under heating reflux condition. The reaction mixture was added water and extracted with ethyl acetate. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residues were subjected to silica gel column chromatography (hexane/ethyl acetate) to obtain 2-(furan-2-yl)-4,5-dimethyloxazole (6.4 g, 40%) as a pale yellow oil.

Workup

  1. temperatureunder heating
  2. temperaturereflux condition
  3. extractionextracted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8aa5af39de994b468a489cac826bb575
Source dataset
uspto-grants-2014_03
Patent number
US08664226B2

Reaction notes

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