Acetic Acid → alpha-(2-fluorophenyl)-N-t-butylnitrone

HRID 636721

Reaction equation

HRID 636721 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][C:11]([N+:14]([O-])=[O:15])([CH3:13])[CH3:12].C(O)(=O)C>C(O)C.[Zn]>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[N+:14]([C:11]([CH3:13])([CH3:12])[CH3:10])[O-:15]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 116722-Methyl-2-nitropropaneHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 85599391alpha-(2-fluorophenyl)-N-t-butylnitrone

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 2-fluorobenzaldehyde (332.3 mg, 2.68 mmol), 1,1-dimethylnitroethane (547.5 mg, 5.31 mmol) and zinc (514.6 mg, 7.87 mmol) in ethanol (3.0 ml) was added acetic acid (940.2 mg, 15.7 mmol) dropwise at 5° C. while stirring. The mixture was stirred at room temperature for 6.5 hours. Zinc acetate in the mixture was filtered off and the filtrate was concentrated and purified by silica gel chromatography (hexane/ethyl acetate=4/1 to 2/1).

Workup

  1. stirringThe mixture was stirred at room temperature for 6.5 hours
  2. filtrationZinc acetate in the mixture was filtered off
  3. concentrationthe filtrate was concentrated
  4. custompurified by silica gel chromatography (hexane/ethyl acetate=4/1 to 2/1)

Sources & evidence

ORD record
ord-61d658cb9eb749bda8fe13737e290f2a
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Linked notes

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