3,4-Dimethoxybenzeneacetonitrile → (z)-2-(3,4-Dimethoxy-phenyl)-3-(3-ethoxy-4-hydroxy-phenyl)-acrylonitrile

HRID 2222334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2222334
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12]COCCOC)[CH:7]=O)[CH3:2].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:24][C:25]#[N:26]>>[CH3:19][O:20][C:21]1[CH:22]=[C:23](/[C:24](=[CH:7]/[C:6]2[CH:9]=[CH:10][C:11]([OH:12])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)/[C:25]#[N:26])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]

Komponenten

3

Edukt 2

HCID 667273,4-DimethoxybenzeneacetonitrileHCID 87761353HCID 87761353, Verbindung

Produkt 1

HCID 10448983(z)-2-(3,4-Dimethoxy-phenyl)-3-(3-ethoxy-4-hydroxy-phenyl)-acrylonitrileAusbeute 37,7 %

Versuchsvorschrift

The hydroxyl group of 3-ethoxy-4-hydroxybenzaldehyde (2.0 g) was protected by use of 2-methoxyethoxymethyl chloride (1.5 g) in accordance with (production process 1), to thereby produce 3-ethoxy-4-methoxyethoxymethoxybenzaldehyde (2.8 g, yield: 91%). The thus-produced 3-ethoxy-4-methoxyethoxymethoxybenzaldehyde (2.8 g) and 3,4-dimethoxybenzyl cyanide (2.0 g) were subjected to condensation in accordance with process A of (production process 2), to thereby yield an MEM form of the target product. Subsequently, the protective group was removed from the MEM form in accordance with (production process 3), to thereby produce the target product (1.35 g, yield: 37%).

Aufarbeitung

  1. customto thereby yield an MEM form of the target product
  2. customSubsequently, the protective group was removed from the MEM form in accordance with (production process 3)

Quellen und Nachweise

ORD-Eintrag
ord-57b98e096a814287923c6713da48c270
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07371773B2

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