Water → Methyl 3-[5-(4-trifluoromethylphenyl)-3-isoxazolyl]benzoate

HRID 1354440노트

반응식

HRID 1354440 반응식
Cl[C:2](=[N:13][OH:14])[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)#[CH:16].C(N(CC)CC)C.O>O1CCCC1>[F:24][C:23]([F:25])([F:26])[C:20]1[CH:19]=[CH:18][C:17]([C:15]2[O:14][N:13]=[C:2]([C:3]3[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=3)[C:6]([O:8][CH3:9])=[O:7])[CH:16]=2)=[CH:22][CH:21]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 43482951-Ethynyl-4-(trifluoromethyl)benzeneHCID 85867392Methyl 3-[chloro(hydroxyimino)methyl]benzoate

생성물 1

HCID 22934533Methyl 3-[5-(4-trifluoromethylphenyl)-3-isoxazolyl]benzoate수율 47.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution (60 ml) of methyl 3-[chloro(hydroxyimino)methyl]benzoate (2.14 g) and 1-ethynyl-4-trifluoromethylbenzene (1.73 g) in tetrahydrofuran was added dropwise a solution (40 ml) of triethylamine(2.79 ml) in tetrahydrofuran under an argon atmosphere at 0° C. This mixture was stirred overnight at room temperature and poured into water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from hexane-ethyl acetate to give methyl 3-[5-(4-trifluoromethylphenyl)-3-isoxazolyl]benzoate (1.64 g, yield 47%) as a colorless crystalline powder. melting point: 139–140° C.

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallized from hexane-ethyl acetate

출처 및 근거

ORD 기록
ord-69690b8c009342c6a70bf0ee561a9f86
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223791B2

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