Ethyl 3-methyl-5-phenyl-1,2-oxazole-4-carboxylate → 3-Methyl-5-phenylisoxazole-4-carboxylic acid

HRID 1063348노트

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HRID 1063348 반응식
[CH3:1][C:2]1[C:6]([C:7]([O:9]CC)=[O:8])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:4][N:3]=1>C(O)C>[CH3:1][C:2]1[C:6]([C:7]([OH:9])=[O:8])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:4][N:3]=1

참가 물질

3

반응물 1

HCID 14011588Ethyl 3-methyl-5-phenyl-1,2-oxazole-4-carboxylate

생성물 1

HCID 27765143-Methyl-5-phenylisoxazole-4-carboxylic acid수율 16.9%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The ethyl 3-methyl-5-phenyl-4-isoxazole carboxylate (1.45 g) obtained in the above reaction was dissolved in ethanol (45 ml) and distilled water (15 ml), potassium hydroxide (1.3 g) was added thereto at room temperature, and the mixture was stirred under heat reflux for 1 hour. After the completion of the reaction, the mixture was concentrated to remove ethanol, distilled water was added thereto, and the mixture was acidified (pH=4) using 1%-aqueous hydrochloric acid. Extraction by liquid separation using dichloromethane and washing with a saturated saline solution were then performed. The product was dried over sodium sulfate followed by concentration and the residue was purified by silica gel column chromatography using a chloroform-methanol elution system. Thus, 3-methyl-5-phenyl-4-isoxazole carboxylic acid (215 mg, yield 16.9%), a starting compound for the Curtius reaction described in Example 1, was obtained.

후처리

  1. distillationdistilled water (15 ml), potassium hydroxide (1.3 g)
  2. additionwas added
  3. temperatureunder heat
  4. temperaturereflux for 1 hour
  5. customAfter the completion of the reaction
  6. concentrationthe mixture was concentrated
  7. customto remove ethanol
  8. distillationdistilled water
  9. additionwas added
  10. extractionExtraction
  11. customby liquid separation
  12. washwashing with a saturated saline solution
  13. dry with materialThe product was dried over sodium sulfate
  14. concentrationfollowed by concentration
  15. customthe residue was purified by silica gel column chromatography
  16. washa chloroform-methanol elution system

출처 및 근거

ORD 기록
ord-e403976419e74f29ae2ca1d687a84e44
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06964975B2

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