Cornforth reagent → 3-(1-Nitro-2-naphthoyl)benzonitrile

HRID 1191303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191303
[OH:1][CH:2]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]=1[N+:21]([O-:23])=[O:22])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[N+:21]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[CH:20][C:11]=1[C:2]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7])=[O:1])([O-:23])=[O:22]

Komponenten

4

Edukt 2

HCID 2724130Cornforth reagentHCID 866904453-[Hydroxy(1-nitronaphthalen-2-yl)methyl]benzonitrile

Produkt 1

HCID 866904463-(1-Nitro-2-naphthoyl)benzonitrileAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-[hydroxy(1-nitronaphthalen-2-yl)methyl]benzonitrile (7.37 g, 24.2 mmol) in dichloromethane (70 mL) was added silica gel (30 g) and pyridinium dichromate (13.7 g, 36.3 mmol), and stirred for 18 hours. The reaction mixture was filtered, and the residue was washed with chloroform. The filtrate was concentrated to dryness, and the residue was recrystallized from ethyl acetate, and washed with hexane to give the titled compound as a pale yellow crystal (6.32 g, yield 86%).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washthe residue was washed with chloroform
  3. concentrationThe filtrate was concentrated to dryness
  4. customthe residue was recrystallized from ethyl acetate
  5. washwashed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-1419e081f6a949c6aec4ed7feba67278
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680110B2

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