Lithium hydroxide, monohydrate → 5-Ethyl-3-phenyl-1,2-oxazole-4-carboxylic acid

HRID 2219327Notes

Reaction equation

HRID 2219327 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:7][O:8][C:9]=1[CH2:10][CH3:11])=[O:4].O[Li].O>C1COCC1.O>[CH2:10]([C:9]1[O:8][N:7]=[C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]=1[C:3]([OH:4])=[O:2])[CH3:11]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57466732HCID 57466732, compound

Product 1

HCID 135451045-Ethyl-3-phenyl-1,2-oxazole-4-carboxylic acidYield 72.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-ethyl-3-phenyl-isoxazole-4-carboxylic acid methyl ester (12.0 g, 51 mmol) in THF (50 mL), was added a solution of LiOH.H2O (10.8 g, 255 mmol) in water (25 mL) in one portion. The reaction mixture was then heated under reflux for 12 h. After cooling to room temperature and concentration, the remaining mixture was extracted with ethyl acetate and dried over sodium sulphate. Evaporation afforded the title compound (8.01 g, 72%) as yellow solid. MS: m/e=218.1 [M+H]+.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureunder reflux for 12 h
  3. concentrationconcentration
  4. extractionthe remaining mixture was extracted with ethyl acetate
  5. dry with materialdried over sodium sulphate
  6. customEvaporation

Sources & evidence

ORD record
ord-4877205193f3444d989c7ce319d59308
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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