Acetic Acid → alpha-(2,4-diflurophenyl)-N-[dimethyl(methoxymethoxymethyl)methyl]nitrone

HRID 636737Notes

Reaction equation

HRID 636737 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][CH2:15][O:16][CH3:17].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][CH2:15][O:16][CH3:17])[O-:20]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 737702,4-DifluorobenzaldehydeHCID 212556992-Methyl-2-nitro-1-(methoxymethoxy)propane

Product 1

HCID 73691529alpha-(2,4-diflurophenyl)-N-[dimethyl(methoxymethoxymethyl)methyl]nitroneYield 64.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2,4-difluorobenzaldehyde (293.3 mg, 2.06 mmol), 2-methyl-2-nitro-1-(methoxymethoxy)propane (382.7 mg, 2.35 mmol) and zinc (266 mg, 4.07 mmol) in ethanol (5 ml) was cooled to 0° C. in ice-water bath. Acetic acid (0.46 ml, 8.0 mmol) was added dropwise to the mixture. The mixture was gradually warmed to room temperature and stirred for 19 hours. The mixture was filtered through Celite® bed and the filtrate was concentrated and purified by silica gel chromatography (hexane/ethyl acetate=4/1) to give the title compound (361.9 mg; 56%).

Workup

  1. filtrationThe mixture was filtered through Celite® bed
  2. concentrationthe filtrate was concentrated
  3. custompurified by silica gel chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-7c8d14fe609c41a4bc7ee26a44e99b1a
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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