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

HRID 405731Notes

Reaction equation

HRID 405731 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].O.[OH-].[Li+]>CO>[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

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57475873Methyl 5-(2,2,2-trifluoroethoxy)pyridine-2-carboxylate

Product 1

HCID 574758545-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Under an atmosphere of nitrogen a solution of 5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester (216 mg, 0.92 mmol) in methanol (1 ml) was treated with a solution of lithium hydroxide monohydrate (78 mg, 1.84 mmol) in methanol (0.1 ml). After stirring for 2 hours the reaction mixture was evaporated at reduced pressure. The residue was treated with hydrochloric acid (1N), the solid material was filtered then washed with water, finally dried at high vacuum. The 5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid was obtained as a white solid (125 mg, 61% of theory).

Workup

  1. customwas evaporated at reduced pressure
  2. additionThe residue was treated with hydrochloric acid (1N)
  3. filtrationthe solid material was filtered
  4. washthen washed with water
  5. customfinally dried at high vacuum

Sources & evidence

ORD record
ord-a2a73a5c8fca492a931b986271e91a6c
Source dataset
uspto-grants-2014_06
Patent number
US08754075B2

Reaction notes

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