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

HRID 1354440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1354440
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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 22934533Methyl 3-[5-(4-trifluoromethylphenyl)-3-isoxazolyl]benzoateAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-69690b8c009342c6a70bf0ee561a9f86
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07223791B2

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