Methanol → 3-Methyl-5-(pyridin-4-yl)-1,2-oxazole-4-carboxylic acid

HRID 60573Notes

Reaction equation

HRID 60573 reaction equation
[CH3:1][C:2]1[C:6]([C:7]([O:9]CC)=[O:8])=[C:5]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[O:4][N:3]=1.C1COCC1.CO.[OH-].[Na+]>O>[CH3:1][C:2]1[C:6]([C:7]([OH:9])=[O:8])=[C:5]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[O:4][N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86680844HCID 86680844, compound

Product 1

HCID 282757673-Methyl-5-(pyridin-4-yl)-1,2-oxazole-4-carboxylic acidYield 57.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 3-methyl-5-(pyridin-4-yl)-1,2-oxazole-4-carboxylate (0.95 g) in a mixed solvent of THF (20 mL)/methanol (10 mL) was added 1N aqueous sodium hydroxide solution (5.0 mL), and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added water, and the mixture was washed with ethyl acetate. The obtained aqueous layer was acidified with 1N hydrochloric acid, sodium chloride was added thereto until the mixture became saturated, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (0.48 g).

Workup

  1. washthe mixture was washed with ethyl acetate
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8447bdb3710e4f36986d4aeb56d6ad00
Source dataset
uspto-grants-2016_09
Patent number
US09440990B2

Reaction notes

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