Sodium Hydroxide → 2-phenyl-1,3-oxazole-4-carboxylic Acid

HRID 1755275Notes

Reaction equation

HRID 1755275 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:9][CH:10]=1)=[O:5])C.[OH-].[Na+]>C1COCC1.CO.CCOC(C)=O>[C:11]1([C:8]2[O:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 571056Ethyl 2-phenyl-1,3-oxazole-4-carboxylate

Product 1

HCID 12347522-phenyl-1,3-oxazole-4-carboxylic AcidYield 84.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Phenyl-oxazole-4-carboxylic acid ethyl ester (500 mg, 2.30 mmol) was dissolved in a mixture of THF (2.3 mL) and MeOH (2.3 mL). To this was added NaOH (10% aqueous, 2.3 mL). The reaction mixture was stirred for 2 h, and was then diluted with EtOAc and washed with 1N HCl The aqueous layer was extracted with EtOAc and the combined organics were dried over Na2SO4, filtered and concentrated to give the product as a white solid (366 mg, 84%).

Workup

  1. washwashed with 1N HCl The aqueous layer
  2. extractionwas extracted with EtOAc
  3. dry with materialthe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2375a725800040b5ab5f592111fdc2d1
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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