Diethyl Ether → 5-Difluoromethympyrazine-2-carboxylic acid

HRID 1693175Notes

Reaction equation

HRID 1693175 reaction equation
FC(F)(F)C(O)=O.[F:8][CH:9]([F:23])[C:10]1[N:11]=[CH:12][C:13]([C:16]([O:18]C(C)(C)C)=[O:17])=[N:14][CH:15]=1.CCOCC.[OH-].[Na+]>ClCCl>[F:23][CH:9]([F:8])[C:10]1[N:11]=[CH:12][C:13]([C:16]([OH:18])=[O:17])=[N:14][CH:15]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 57475685t-Butyl 5-difluoromethylpyrazine-2-carboxylate

Product 1

HCID 574685755-Difluoromethympyrazine-2-carboxylic acidYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 mL) was added to a solution of t-butyl 5-difluoromethylpyrazine-2-carboxylate (175 mg) in dichloromethane (1 mL), and the mixture was stirred at room temperature for five hours. Ether and 5 N sodium hydroxide were added to the reaction solution. The aqueous layer was separated and made acidic with 5 N hydrochloric acid. Ethyl acetate was added to the aqueous layer, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the insoluble matter was separated by filtration. The filtrate was concentrated to obtain the title compound (100 mg).

Workup

  1. customThe aqueous layer was separated
  2. additionEthyl acetate was added to the aqueous layer
  3. customthe organic layer was separated
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe insoluble matter was separated by filtration
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e3c9665299b94bf1a9e7f6037f378ba1
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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