Sodium Methoxide → 4-[1-Methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylaniline

HRID 1952261Notes

Reaction equation

HRID 1952261 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([C:9](F)([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[C:6]([CH2:19][CH2:20][CH3:21])=[CH:5][C:3]=1[NH2:4].[CH3:22][O-:23].[Na+]>CO>[CH3:22][O:23][C:9]([C:7]1[C:6]([CH2:19][CH2:20][CH3:21])=[CH:5][C:3]([NH2:4])=[C:2]([CH3:1])[CH:8]=1)([C:14]([F:16])([F:15])[F:17])[C:10]([F:12])([F:11])[F:13]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 866298542-Methyl-5-n-propyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline

Product 1

HCID 866298554-[1-Methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylanilineYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Methyl-5-n-propyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline (1.6 g, 5 mmol) was dissolved in a 28% solution (9.6 g) of sodium methoxide in methanol, and the mixture was heated under reflux for 3 hr. After allowing to cool, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give the desired compound (1.31 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-cf7e4a7aaaa445e28c9718c95b5413e5
Source dataset
uspto-grants-2013_03
Patent number
US08404861B2

Reaction notes

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