Lithium Hydroxide → 5-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acid

HRID 1186193Notes

Reaction equation

HRID 1186193 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[CH:7][N:6]=1)=[O:4].[Li+].[OH-]>CO.O>[F:16][C:13]([F:14])([F:15])[CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57475873Methyl 5-(2,2,2-trifluoroethoxy)pyridine-2-carboxylate

Product 1

HCID 574758545-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acidYield 61.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester (216 mg) in MeOH (1 ml) was treated with a solution of LiOH (78 mg) in water (0.1 ml) and stirring was continued at 22° C. for 2 h. The solution was evaporated and the residue triturated with 1 N aqueous HCl. The suspension was filtered, the residue washed with water and dried to give 5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (125 mg) as a white solid. MS (ISN): m/z=220.1 [M−H]−.

Workup

  1. customThe solution was evaporated
  2. customthe residue triturated with 1 N aqueous HCl
  3. filtrationThe suspension was filtered
  4. washthe residue washed with water
  5. customdried

Sources & evidence

ORD record
ord-b88fa2502d8a41a0ac992db82c1903cb
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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