Potassium Carbonate → Methyl 5-(2,2,2-trifluoroethoxy)pyridine-2-carboxylate

HRID 509603Notes

Reaction equation

HRID 509603 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][N:6]=1)=[O:4].[F:12][C:13]([F:21])([F:20])[CH2:14]OS(C)(=O)=O.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:14][C:13]([F:21])([F:20])[F:12])=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5565652,2,2-Trifluoroethyl MethanesulfonateHCID 4715126Methyl 5-hydroxypyridine-2-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-Hydroxy-pyridine-2-carboxylic acid methyl ester 2 (0.5 g, 3.26 mmol), methanesulfonic acid 2,2,2-trifluoro-ethyl ester (1.0 g, 5.34 mmol) and K2CO3 (1.4 g, 9.8 mmol) in acetonitrile (50 mL) was stirred overnight. The solid was filtered off and the filtrate was concentrated. The residue was purified by column chromatography (eluting with hexane and ethyl acetate 1:1) to afford 5-(2,2,2-Trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester 3 as a white solid. Yield: 0.437 g, 57.1%.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography (eluting with hexane and ethyl acetate 1:1)

Sources & evidence

ORD record
ord-5453deb679c446b0a23e3b94f3fee7b5
Source dataset
uspto-grants-2015_08
Patent number
US09096587B2

Reaction notes

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