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Ammonium Chloride → 3-[3-Chloro-4-(1-hydroxyethyl)phenyl]-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

HRID 885801
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 885801
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[CH2:14][C:13]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)([C:15]([F:18])([F:17])[F:16])[O:12][N:11]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:27][Mg]Br.[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[CH2:14][C:13]([C:19]3[CH:20]=[C:21]([Cl:26])[CH:22]=[C:23]([Cl:25])[CH:24]=3)([C:15]([F:18])([F:17])[F:16])[O:12][N:11]=2)[CH:7]=[CH:6][C:3]=1[CH:4]([OH:5])[CH3:27]
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Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 866315512-Chloro-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]benzaldehydeHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 866315533-[3-Chloro-4-(1-hydroxyethyl)phenyl]-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283
Diethyl Ether
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a solution of 1.4 g of 2-chloro-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]benzaldehyde in 50 mL of diethyl ether under nitrogen atmosphere, 6.6 mL of a solution (0.87 mol/L) of methyl magnesium bromide in tetrahydrofuran was added dropwise with stirring at room temperature. After the completion of the addition dropwise, the mixture was continued to stir under reflux with heating further for 30 minutes. After the completion of the reaction, 5 mL of ammonium chloride aqueous solution was added in the reaction mixture under cooling with ice and with stirring, the mixture was extracted with ethyl acetate (50 mL×1), the organic phase was washed with water (30 mL×2), and dehydrated with and dried over saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order, and then the solvent was distilled off under reduced pressure to obtain 1.5 g of the aimed product as pale yellow resinous substance.

Aufarbeitung

  1. additionAfter the completion of the addition dropwise
  2. stirringto stir
  3. temperatureunder reflux
  4. temperaturewith heating further for 30 minutes
  5. additionwas added in the reaction mixture
  6. temperatureunder cooling with ice
  7. stirringwith stirring
  8. extractionthe mixture was extracted with ethyl acetate (50 mL×1)
  9. washthe organic phase was washed with water (30 mL×2)
  10. dry with materialdried over saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order
  11. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b533911b738d4961a1d94bb92065e6fd
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08242283B2

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