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

HRID 636746Notes

Reaction equation

HRID 636746 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+:23]([O-])=[O:24])([CH3:22])[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.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+:23]([C:12]([CH3:22])([CH3:11])[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[O-:24]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 737702,4-DifluorobenzaldehydeHCID 212556982-Methyl-2-nitro-1-benzyloxypropane

Product 1

HCID 73197188alpha-(2,4-Difluorophenyl)-n-[dimethyl(benzyloxymethyl)methyl]nitroneYield 48%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2,4-difluorobenzaldehyde (443.7 mg, 3.12 mmol), 2-methyl-2-nitro-1-benzyloxypropane (639.4 mg, 3.06 mmol) and zinc (326.4 mg, 4.99 mmol) in ethanol (6 ml) was cooled to 0° C. in ice-water bath. Acetic acid (0.57 ml, 9.9 mmol) was added dropwise to the mixture. The mixture was gradually warmed to room temperature and stirred for 7 hours. The mixture was filtered through Celite® bed and the filtrate was concentrated and purified by silica gel chromatography (hexane/ethyl acetate=10/1-4/1) to give the title compound (468.8 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=10/1-4/1)

Sources & evidence

ORD record
ord-f375c44571e641538adcb015f072a831
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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