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

HRID 517047Notes

Reaction equation

HRID 517047 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-2927ef12c38141af979b9927fe441ae6
Source dataset
uspto-grants-2015_08
Patent number
US09115098B2

Reaction notes

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