Ammonium Chloride → {4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-phenyl}-oxo-acetic acid methyl ester

HRID 1022848

Reaktionsgleichung

Reaktionsgleichung von HRID 1022848
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)=[CH:4][C:3]=1[CH3:25].C([Li])(C)(C)C.[Mg+2].[Br-].[Br-].[Cl-].[CH3:35][O:36][C:37](=[O:41])[C:38](O)=[O:39].[NH4+].[Cl-]>C1COCC1.CCCCC>[CH3:35][O:36][C:37](=[O:41])[C:38]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:18]=[C:19]([Cl:24])[CH:20]=[C:21]([Cl:23])[CH:22]=3)([C:13]([F:15])([F:16])[F:14])[O:10][N:9]=2)=[CH:4][C:3]=1[CH3:25])=[O:39]

Komponenten

8

Edukt 5

HCID 25517Ammonium ChlorideHCID 82241Magnesium BromideHCID 231598123-(4-Bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazoleHCID 86640482Oxalic acid monomethyl ester chlorideHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 67444292{4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-phenyl}-oxo-acetic acid methyl esterAusbeute 17,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8003PentaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 3-(4-bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (1.00 g) in THF (40 mL) was added tert-butyllithium (16.2 mL of a 1.6 M solution in pentane) at −78° C. After 10 min at this temperature, MgBr2 (0.15 M in THF, 10.3 mL) was added dropwise and left for another 15 min. Oxalic acid methylester chloride (284 mg) was added and the mixture was stirred at −78° C. for 1 h before it was allowed to warm to room temperature over night. Saturated aqueous NH4Cl solution was added and the mixture was extracted with MTBE. The organic layer was separated, dried (Na2SO4) and concentrated in vacuum. The residue was purified by flash chromatography on silica gel to yield the title compound (167 mg, 16%).

Aufarbeitung

  1. temperatureto warm to room temperature over night
  2. extractionthe mixture was extracted with MTBE
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuum
  6. customThe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4f0ff100a73a498daab51799e8357975
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722673B2

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