Diethyl Ether → Ethyl 5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylate

HRID 585072

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HRID 585072 반응식
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:13][N:12]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10]2)=[CH:5][CH:4]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.CCOCC>C1(C)C=CC=CC=1>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=2)=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 22064077Ethyl 5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole-3-carboxylate

생성물 1

HCID 22064085Ethyl 5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylate

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
75 °C

실험 절차

A solution of ethyl 5-[4-(trifluoromethyl)phenyl]-4,5-dihydroisoxazole-3-carboxylate (3.3 g) was stirred in toluene (15 ml), and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (1.00 g) was then added in portions, followed by a portion of 3A molecular sieves, and the resulting mixture was stirred at 75° C. for 2 days. After cooling, ether was added and the mixture filtered through a layer anhydrous sodium sulfate. Solvent was evaporated under reduced pressure, and the residue was purified by column chromatography, to provide ethyl 5-[4-(trifluoromethyl)phenyl]isoxazole-3-carboxylate, a compound of formula (23).

후처리

  1. temperatureAfter cooling
  2. filtrationthe mixture filtered through a layer anhydrous sodium sulfate
  3. customSolvent was evaporated under reduced pressure
  4. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-4e0b8617c7a6461baafa3bd8f99cbd27
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06930111B2

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