Tert-Butyl nitrite → 2-(Hydroxyimino)-2-phenyl-1-p-tolylethanone

HRID 1430594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1430594
[C:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:17](OC(C)(C)C)=[O:18].[O-]CC.[Na+]>CCO>[OH:18][N:17]=[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)=[O:9]

Komponenten

5

Edukt 3

HCID 10906Tert-Butyl nitriteHCID 2280161-(4-Methylphenyl)-2-phenylethan-1-oneHCID 2723922Sodium ethoxide

Produkt 1

HCID 866581402-(Hydroxyimino)-2-phenyl-1-p-tolylethanoneAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-phenyl-1-p-tolylethanone (5.0 g, 23.78 mmol) in EtOH (475.0 mL) at room temperature was added dropwise tert-butyl nitrite (5.5 mL, 46.2 mmol) followed by sodium ethoxide (4.07 g, 59.8 mmol). The reaction was stirred at room temperature overnight and concentrated under reduced pressure. The residue was dissolved in EtOAc, washed with H2O, brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography to give the title compound as an orange oil (5.31 g). LCMS m/z=239.9 [M+H]+.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with H2O, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-81312b9822384ab5b5a605dca10facff
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940891B2

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