Water → 2-(4-Benzyloxy-3-methoxy-phenyl)-vinylamine

HRID 2414820

Reaktionsgleichung

Reaktionsgleichung von HRID 2414820
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]=[CH:20][N+:21]([O-])=O)=[CH:17][C:16]=1[O:26][CH3:27])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[CH2:7]([O:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]=[CH:20][NH2:21])=[CH:17][C:16]=1[O:26][CH3:27])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 158282-Methoxy-4-(2-nitroethenyl)-1-(phenylmethoxy)benzeneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 576415372-(4-Benzyloxy-3-methoxy-phenyl)-vinylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A stirred suspension of LAH (8.0 g, 0.21 mol) in THF (300 mL) is cooled in an ice bath and a solution of 4-benzyloxy-3-methoxynitrostyrene (15.0 g, 52.6 mmol) in THF (300 mL) is added dropwise. The green reaction mixture is allowed to warm to room temperature over 0.5 h, and is then refluxed for 4 h. The grey reaction mixture is treated successively with water (8 mL), 15% aqueous NaOH (8 mL), and water (24 mL). The resulting gray suspension is stirred at 50° C. for 20 min. The resulting yellow suspension is filtered, and the residue is washed with EtOAc. The combined filtrates are evaporated to provide the title compound as yellow oil which is used without further purification.

Aufarbeitung

  1. temperatureis cooled in an ice bath
  2. temperatureis then refluxed for 4 h
  3. filtrationThe resulting yellow suspension is filtered
  4. washthe residue is washed with EtOAc
  5. customThe combined filtrates are evaporated

Quellen und Nachweise

ORD-Eintrag
ord-a9ea6218e442440e89e5650b0dee9a1d
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06815451B2

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