Acetic Acid → alpha-(2,4-Difluorophenyl)-n-[dimethyl(acetoxymethyl)methyl]nitrone

HRID 636739Notes

Reaction equation

HRID 636739 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]([N+:19]([O-])=[O:20])([CH3:18])[CH2:13][O:14][C:15](=[O:17])[CH3:16].C(O)(=O)C>C(O)C.[Zn]>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[N+:19]([C:12]([CH3:18])([CH3:11])[CH2:13][O:14][C:15](=[O:17])[CH3:16])[O-:20]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 737702,4-DifluorobenzaldehydeHCID 212556952-Methyl-2-nitro-1-acetoxypropane

Product 1

HCID 86756464alpha-(2,4-Difluorophenyl)-n-[dimethyl(acetoxymethyl)methyl]nitroneYield 48.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2,4-difluorobenzaldehyde (428.2 mg, 3.01 mmol), 2-methyl-2-nitro-1-acetoxypropane (467.8 mg, 2.90 mmol) and zinc (321.7 mg, 4.92 mmol) in ethanol (5 ml) was cooled to 0° C. in ice-water bath. Acetic acid (0.57 ml, 9.9 mmol) was added dropwise to the mixture and was warmed to room temperature and stirred for 16 hours. The mixture was filtered through Celite® bed and the filtrate was concentrated and purified by silica gel chromatography (hexane/ethyl acetate=2/1) to give the title compound (380.8 mg; 48%).

Workup

  1. filtrationThe mixture was filtered through Celite® bed
  2. concentrationthe filtrate was concentrated
  3. custompurified by silica gel chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-ffe2f041b6a24073936ebf65d2fd60d5
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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