Methyl 3-methyl-5-(3-methylphenyl)-4-isoxazole carboxylate → 3-Methyl-5-(3-methylphenyl)-1,2-oxazole-4-carboxylic acid

HRID 1063351Notes

Reaction equation

HRID 1063351 reaction equation
[CH3:1][C:2]1[C:6]([C:7]([O:9]C)=[O:8])=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=2)[O:4][N:3]=1>O1CCCC1>[CH3:1][C:2]1[C:6]([C:7]([OH:9])=[O:8])=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=2)[O:4][N:3]=1

Participants

3

Reactant 1

HCID 22279613Methyl 3-methyl-5-(3-methylphenyl)-4-isoxazole carboxylate

Product 1

HCID 222795143-Methyl-5-(3-methylphenyl)-1,2-oxazole-4-carboxylic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-methyl-5-(3-methylphenyl)-4-isoxazole carboxylate (183 mg) was dissolved in tetrahydrofuran/distilled water=4/1 (2 ml). Lithium hydroxide (66.5 mg) was added at room temperature, and the mixture was stirred at that temperature for 20 hours. After the completion of the reaction, 5%-aqueous hydrochloric acid was added to acidify the system, and the reaction product was extracted by liquid separation using chloroform and washed with saturated aqueous solution of sodium chloride. The product was dried over sodium sulfate to concentrate and the residue was dried using a vacuum pump. Thus, a useful intermidiate, i.e., 3-methyl-5-(3-methylphenyl)-4-isoxazole carboxylic acid (169 mg, yield 98%) was obtained.

Workup

  1. distillationdistilled water=4/1 (2 ml)
  2. additionLithium hydroxide (66.5 mg) was added at room temperature
  3. customAfter the completion of the reaction, 5%-aqueous hydrochloric acid
  4. additionwas added
  5. extractionthe reaction product was extracted by liquid separation
  6. washwashed with saturated aqueous solution of sodium chloride
  7. dry with materialThe product was dried over sodium sulfate
  8. concentrationto concentrate
  9. customthe residue was dried

Sources & evidence

ORD record
ord-cace0fdcf82842749459864c3f4ef8d8
Source dataset
uspto-grants-2005_11
Patent number
US06964975B2

Reaction notes

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