Acetic Acid → alpha-(2,6-difluorophenyl)-N-t-butylnitrone

HRID 636724Notes

Reaction equation

HRID 636724 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=O.[CH3:11][C:12]([N+:15]([O-])=[O:16])([CH3:14])[CH3:13].C(O)(=O)C>C(O)C.[Zn]>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=[N+:15]([C:12]([CH3:14])([CH3:13])[CH3:11])[O-:16]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 116722-Methyl-2-nitropropaneHCID 1362842,6-Difluorobenzaldehyde

Product 1

HCID 57348010alpha-(2,6-difluorophenyl)-N-t-butylnitrone

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 2,6-difluorobenzaldehyde (374.7 mg, 2.64 mmol), 1,1-dimethylnitroethane (541.6 mg, 5.25 mmol) and zinc (517.0 mg, 7.91 mmol) in ethanol (3.0 ml) was added acetic acid (940.5 mg, 15.7 mmol) dropwise at 5° C. while stirring. The mixture was stirred at room temperature for 5 hours. Zinc acetate in the mixture was filtered off and the filtrate was concentrated and purified by silica gel chromatography (hexane/ethyl acetate=5/2-2/1).

Workup

  1. stirringThe mixture was stirred at room temperature for 5 hours
  2. filtrationZinc acetate in the mixture was filtered off
  3. concentrationthe filtrate was concentrated
  4. custompurified by silica gel chromatography (hexane/ethyl acetate=5/2-2/1)

Sources & evidence

ORD record
ord-d4f9419bd857404c9644ae07cde063e9
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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