Methanol → 2-((5-(1-(((4-(Trifluoromethyl)benzyl)oxy)imino)ethyl)pyridin-2-yl)oxy)acetic acid

HRID 68312Notes

Reaction equation

HRID 68312 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:25]=[CH:24][C:6]([CH2:7][O:8][N:9]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]([O:22]C)=[O:21])=[N:16][CH:17]=2)[CH3:11])=[CH:5][CH:4]=1.CO.O.[OH-].[Li+]>C1COCC1>[F:26][C:2]([F:1])([F:27])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][N:9]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]([OH:22])=[O:21])=[N:16][CH:17]=2)[CH3:11])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 86699621Methyl 2-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)pyridin-2-yl)oxy)acetate

Product 1

HCID 765282142-((5-(1-(((4-(Trifluoromethyl)benzyl)oxy)imino)ethyl)pyridin-2-yl)oxy)acetic acidYield 88.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of step 3 (2.0 gm, 5.2 mmoles) in a mixture of THF (12 mL), methanol (4 mL) and water (4 mL), lithium hydroxide (440 mg, 10.5 mmoles) was added and the reaction mixture was stirred at ambient temperature for 4 hours. The solvents were evaporated under reduced pressure. The residue was dissolved in water, acidified with 1N HCl and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evapourated under reduced pressure to yield 1.7 gm (88%) of title product as white solid.

Workup

  1. additionwas added
  2. customThe solvents were evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with ethyl acetate
  5. extractionThe combined ethyl acetate extract
  6. washwas washed with water & brine
  7. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-d44a5704160a4e7ca4c60ca2b495b5ab
Source dataset
uspto-grants-2014_09
Patent number
US08822414B2

Reaction notes

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