O-Methylhydroxylamine → Phenyl(4-(trifluoromethyl)phenyl)methanone O-methyl oxime

HRID 1622569

Reaktionsgleichung

Reaktionsgleichung von HRID 1622569
[C:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][O:20][NH2:21].CCOC(C)=O>N1C=CC=CC=1>[CH3:19][O:20][N:21]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 4113O-Methylhydroxylamine2×HCID 8857Ethyl AcetateHCID 697674-(Trifluoromethyl)benzophenone

Produkt 1

HCID 76047680Phenyl(4-(trifluoromethyl)phenyl)methanone O-methyl oximeAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a 100-mL round-bottomed flask, phenyl(4-(trifluoromethyl)phenyl)-methanone (1.0105 g, 4.039 mmol) and methoxyamine (0.4208 g, 5.038 mmol) were dissolved in pyridine (10 mL). The mixture was stirred at rt overnight. Additional methoxyamine (0.1625 g) was added, and the solution was stirred at rt for 7 h. EtOAc was added and the organic phase was washed with water, 1 N HCl (2×), water, and then with brine. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo to afford a clear oil. The oil thus obtained was purified by Biotage (EtOAc/hexanes 0-20%) to afford the title compound (1.12 g, 99.4%) as a clear oil.

Aufarbeitung

  1. stirringthe solution was stirred at rt for 7 h
  2. washthe organic phase was washed with water, 1 N HCl (2×), water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a clear oil
  7. customThe oil thus obtained
  8. customwas purified by Biotage (EtOAc/hexanes 0-20%)

Quellen und Nachweise

ORD-Eintrag
ord-329d0f7369864518b4df91bcd748e839
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778941B2

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