Chlorosuccinimide → 3-(2-Chlorophenyl)-5-((2,6-difluorobenzyloxy)methyl)-5-methyl-4,5-dihydroisoxazole

HRID 58942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58942
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH:4]=[N:5][OH:6].ClN1C(=O)CCC1=O.C([O-])(O)=O.[Na+].[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:26]=1[CH2:32][O:33][CH2:34][C:35]([CH3:37])=[CH2:36]>ClCCCl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]1[CH2:36][C:35]([CH2:34][O:33][CH2:32][C:26]2[C:27]([F:31])=[CH:28][CH:29]=[CH:30][C:25]=2[F:24])([CH3:37])[O:6][N:5]=1

Komponenten

9

Edukt 4

HCID 31398ChlorosuccinimideHCID 96239o-ChlorobenzaldoximeHCID 516892Sodium BicarbonateHCID 112640711,3-Difluoro-2-((2-methylallyloxy)methyl)benzene

Produkt 1

HCID 903293043-(2-Chlorophenyl)-5-((2,6-difluorobenzyloxy)methyl)-5-methyl-4,5-dihydroisoxazoleAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 111,2-DichloroethaneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

224 mg of 2-chlorobenzaldehyde oxime was dissolved in 4 mL of 1,2-dichloroethane, and then, 230 mg of N-chlorosuccinimide and 0.4 mL of dimethylformamide were slowly added thereto at a temperature of 0° C. The reaction mixture was stirred at room temperature for 1 hour, and then, the reaction state was confirmed by TLC. When the oxime, which was a starting material, disappeared, the reaction mixture was cooled to a temperature 0° C., and then, 182 mg of NaHCO3, 27 mg of tetrabutylammonium iodide, and 342 mg of 1,3-difluoro-2-((2-methylallyloxy)methyl)benzene were sequentially, slowly added thereto. The reaction mixture was stirred at room temperature overnight, and then, diluted with dichloromethane and then washed with water, and the obtained organic layer was dried by using magnesium sulfate and concentrated, and the concentrate was separated by silicagel column chromatography to obtain 400 mg of 3-(2-chlorophenyl)-5-((2,6-difluorobenzyloxy)methyl)-5-methyl-4,5-dihydroisoxazole.

Aufarbeitung

  1. customat a temperature of 0° C
  2. temperaturethe reaction mixture was cooled to a temperature 0° C.
  3. additionslowly added
  4. stirringThe reaction mixture was stirred at room temperature overnight
  5. washwashed with water
  6. customthe obtained organic layer was dried
  7. concentrationconcentrated
  8. customthe concentrate was separated by silicagel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-48619173a53248a19f95cec802601166
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439432B2

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