Methanol → HCID 66803012, compound

HRID 341504Notes

Reaction equation

HRID 341504 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12]C)=[O:11])=[N:8][CH:9]=1.[OH-].[K+:17].CO>O>[F:15][C:2]([F:1])([F:14])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([O-:12])=[O:11])=[N:8][CH:9]=1.[K+:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium Hydroxide2×HCID 66803197HCID 66803197, compound

Product 1

HCID 66803012HCID 66803012, compoundYield 122%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of methyl 5-(trifluoromethoxy)pyridine-2-carboxylate (0.313 g, 1.41 mmol), potassium hydroxide (0.076 g, 1.35 mmol) in a 5:1 MeOH:water mixture (3 mL) was stirred at room temperature for 1 h. Additional potassium hydroxide (0.015 g, 0.267 mmol) in water (0.2 mL) was added and the mixture was stirred at room temperature for 1 h. The reaction mixture was evaporated to dryness and azeotroped twice with toluene to give the potassium 5-(trifluoromethoxy)pyridine-2-carboxylate intermediate (404 mg 100%). A fraction of this intermediate (0.173 g, 0.706 mmol) was dissolved in oxalyl chloride (4 mL) and the mixture was stirred at room temperature for 2 h before being evaporated to dryness and used without further purification in the next step.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customazeotroped twice with toluene

Sources & evidence

ORD record
ord-6a896b8bf5a642ac8165eacd3a9cda1d
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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