1-Propanol → 2-(2,5-dimethylphenoxymethyl)phenyl 3-methylisoxazol-5-yl ketone O-methyloxime

HRID 279445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 279445
C(O)CC.Cl.[CH3:6][O:7][NH2:8].[CH3:9][C:10]1[CH:14]=[C:13]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][O:24][C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:26]=2[CH3:32])=O)[O:12][N:11]=1>O>[CH3:6][O:7][N:8]=[C:15]([C:13]1[O:12][N:11]=[C:10]([CH3:9])[CH:14]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][O:24][C:25]1[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:26]=1[CH3:32]

Komponenten

5

Edukt 3

HCID 10311-PropanolHCID 521874O-Methylhydroxylamine hydrochlorideHCID 226246042-(2,5-Dimethylphenoxymethyl)phenyl 3-methylisoxazol-5-yl ketone

Produkt 1

HCID 542536932-(2,5-dimethylphenoxymethyl)phenyl 3-methylisoxazol-5-yl ketone O-methyloximeAusbeute 42,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

n-Propanol (2 ml) and methoxyamine hydrochloride (0.25 g, 3 mmol) were added to 2-(2,5-dimethylphenoxymethyl)phenyl 3-methylisoxazol-5-yl ketone (0.33 g, 1 mmol), and the mixture was stirred under reflux for 15 hours. After completion of the reaction, water (200 ml) was added, the mixture was extracted with dichloromethane. The dichloromethane layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give isomer A (0.18 g, 51.4%, as colorless crystals) and isomer B (0.15 g, 42.8%, as colorless crystals) of 2-(2,5-dimethylphenoxymethyl)phenyl 3-methylisoxazol-5-yl ketone O-methyloxime. One of the isomers A and B is the E-isomer and the other is Z-isomer.

Aufarbeitung

  1. temperatureunder reflux for 15 hours
  2. additionwas added
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3523d9d721fb44fab64c2c6674ad699f
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362212B1

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