Ethanol → 5-(2,2,2-Trifluoroethoxy)pyrazine-2-carboxylic acid

HRID 1842235Notes

Reaction equation

HRID 1842235 reaction equation
[OH-].[Na+].C(O)C.[F:6][C:7]([F:21])([F:20])[CH2:8][O:9][C:10]1[N:11]=[CH:12][C:13]([C:16]([O:18]C)=[O:17])=[N:14][CH:15]=1.O>C1COCC1.C(OCC)(=O)C>[F:21][C:7]([F:6])([F:20])[CH2:8][O:9][C:10]1[N:11]=[CH:12][C:13]([C:16]([OH:18])=[O:17])=[N:14][CH:15]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 57827340Methyl 5-(2,2,2-trifluoroethoxy)pyrazine-2-carboxylate

Product 1

HCID 578276925-(2,2,2-Trifluoroethoxy)pyrazine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 5 N sodium hydroxide solution (3 mL) and ethanol (3 mL) were added to a solution of methyl 5-(2,2,2-trifluoroethoxy)pyrazine-2-carboxylate obtained in Preparation Example 50-(1) (197 mg) in THF (5 mL), and the mixture was heated under reflux for 15 minutes. After returning to room temperature, water and ethyl acetate were added and the aqueous layer was separated. The aqueous layer was adjusted to pH 1 with hydrochloric acid, and ethyl acetate was added to the aqueous layer. The organic layer was separated and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to obtain the title compound (87 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 minutes
  3. customAfter returning to room temperature
  4. customthe aqueous layer was separated
  5. additionwas added to the aqueous layer
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c3ee4681a00740f7aa26966669ba97b2
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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