2-(4-tert-Butylphenoxy)ethanol → 2-Methyl-3-methoxy-4-[2-(4-tert-butylphenoxy)ethoxy]pyridine

HRID 1017

Reaktionsgleichung

Reaktionsgleichung von HRID 1017
[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[C:11]([C:15]1[CH:24]=[CH:23][C:18]([O:19][CH2:20][CH2:21][OH:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].[H-].[Na+].[Cl-].[NH4+]>CS(C)=O>[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:22][CH2:21][CH2:20][O:19][C:18]2[CH:23]=[CH:24][C:15]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:16][CH:17]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 4

HCID 128412-(4-tert-Butylphenoxy)ethanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 105830464-Chloro-3-methoxy-2-methylpyridine

Produkt 1

HCID 196940232-Methyl-3-methoxy-4-[2-(4-tert-butylphenoxy)ethoxy]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 1.57 g (10 mmol) of 2-methyl-3-methoxy-4-chloropyridine, 2.52 g (13 mmol) of 2-(4-tert-butylphenoxy)ethanol and 15 ml of DMSO is added dropwise at 25° C. to 0.36 g (12 mmol) of NaH (80% strength) in 25 ml of DMSO. The mixture is then stirred at 60° C. for 5 hours. For working up, saturated ammonium chloride solution is added at 20° to 25° C. and the mixture is extracted with ethyl acetate. The reaction product is purified by chromatography (SiO2 ; EtOAc). Yield: 2.63 g (74.9%); m.p.: 84° to 87° C.

Aufarbeitung

  1. extractionthe mixture is extracted with ethyl acetate
  2. customThe reaction product is purified by chromatography (SiO2 ; EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-81b10c28bd9c47d5984b354d59da9d19
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723450

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