2-(4-methoxyphenyl)-4,5-dimethyloxazole N-oxide → 2-(4-Methoxy-phenyl)-4,5-dimethyl-oxazole

HRID 1905516Notes

Reaction equation

HRID 1905516 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]([CH3:16])=[C:12]([CH3:15])[N+:13]=2[O-])=[CH:5][CH:4]=1>C(O)(=O)C.[Zn]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][C:11]([CH3:16])=[C:12]([CH3:15])[N:13]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 200640242-(4-methoxyphenyl)-4,5-dimethyloxazole N-oxide

Product 1

HCID 189829612-(4-Methoxy-phenyl)-4,5-dimethyl-oxazoleYield 80.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc dust (325 mesh, 60 g) was added in portions over 15 minutes to a solution of 43.8 g of 2-(4-methoxyphenyl)-4,5-dimethyloxazole N-oxide in 400 ml of acetic acid, stirred and heated on a steam bath. After an additional 15 minutes of heating, the reaction mixture was filtered and concentrated in vacuo. The residue was stirred with concentrated ammonium hydroxide and ethyl acetate. The layers were separated, the aqueous layer extracted with ethyl acetate, and the combined ethyl acetate solutions dried and concentrated to yield 32.6 g of 2-(4-methoxyphenyl)-4,5-dimethyloxazole as a yellow oil.

Workup

  1. temperatureheated on a steam bath
  2. temperatureAfter an additional 15 minutes of heating
  3. filtrationthe reaction mixture was filtered
  4. concentrationconcentrated in vacuo
  5. stirringThe residue was stirred with concentrated ammonium hydroxide and ethyl acetate
  6. customThe layers were separated
  7. extractionthe aqueous layer extracted with ethyl acetate
  8. dry with materialthe combined ethyl acetate solutions dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d3bf33fadde04c1fbeb34af26d08bf45
Source dataset
uspto-grants-1989_06
Patent number
US04843087

Reaction notes

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