Methanol → HCID 59570987, compound

HRID 2192930Notes

Reaction equation

HRID 2192930 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][O:8][C:9]([CH3:23])([CH3:22])[CH2:10][O:11][C:12]2[N:13]=[CH:14][C:15]([C:18]([O:20]C)=[O:19])=[N:16][CH:17]=2)=[CH:5][CH:4]=1.[OH-].[Na+].CO.C1COCC1>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([CH3:23])([CH3:22])[CH2:10][O:11][C:12]2[N:13]=[CH:14][C:15]([C:18]([OH:20])=[O:19])=[N:16][CH:17]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59571074HCID 59571074, compound

Product 1

HCID 59570987HCID 59570987, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 5-{2-[(4-methoxybenzyl)oxy]-2-methylpropoxy}pyrazine-2-carboxylate (3.5 g), 1 M aqueous sodium hydroxide solution (35 mL), methanol (35 mL), and THF (35 mL) was stirred at room temperature for 1 hour. To the reaction mixture was added water, followed by washing with ethyl acetate. To the aqueous layer was added 1 M hydrochloric acid to adjust the pH to 4, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 5-{2-[(4-methoxybenzyl)oxy]-2-methylpropoxy}pyrazine-2-carboxylic acid (2.5 g) as a pale yellow solid.

Workup

  1. washby washing with ethyl acetate
  2. additionTo the aqueous layer was added 1 M hydrochloric acid
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ebc1c939e1ee42e3b5540e04c84e1f3e
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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