3,5-Dimethoxybenzaldehyde → (3,5-Dimethoxy-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanol

HRID 971019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 971019
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH2:11][CH3:12])[CH:3]=1.C([Li])CCC.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:28][CH3:29])[CH:27]=1)[CH:23]=[O:24].COC1C=C(C(C2C=CC=C(OC)C=2)=CC#N)C=C(OC)C=1>>[CH3:29][O:28][C:26]1[CH:25]=[C:22]([CH:23]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH2:11][CH3:12])[CH:3]=2)[OH:24])[CH:21]=[C:20]([O:19][CH3:18])[CH:27]=1

Komponenten

5

Edukt 4

HCID 817473,5-DimethoxybenzaldehydeHCID 217726904-Bromo-2-ethoxy-1-methoxybenzeneHCID 692052993-(3,5-Dimethoxy-phenyl)-3-(3-methoxy-phenyl)-acrylonitrileHCID 178418339Butyllithium

Produkt 1

HCID 69202471(3,5-Dimethoxy-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanolAusbeute 80 %

Versuchsvorschrift

4-bromo-2-ethoxy-1-methoxybenzene (0.66 g, 2.86 mmol), n-butyl lithium (1.14 ml, 2.86 mmol), and 3,5-dimethoxybenzaldehyde (0.43 g, 2.60 mmol) were treated in the same manner as described above for the synthesis of 3-(3,5-dimethoxy-phenyl)-3-(3-methoxy-phenyl)-acrylonitrile. The crude was purified via flash colurn chromatography (20% EtOAc in hexane gradient to 50% EtOAc in hexane in about 40 min.) to give (3,5-dimethoxy-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanol as an off-white solid (0.66 g, 80%): 1HNMR (CDCl3) δ 6.92-6.80 (m, 3H, Ar), 6.54 (d, J=2 Hz, 2H, Ar), 6.36 (t, J=2 Hz, 1H, Ar), 5.70 (d, J=3 Hz, 1H, CHOH), 4.07 (q, J=6 Hz, 2H, CH2CH3), 3.85 (s, 3H, OCH3), 3.76 (s, 6H, 2OCH3), 2.19 (d, J=3 Hz, 1H, OH), 1.44 (t, J=7 Hz, 3H, CH2CH3). The product was carried over to the next step.

Aufarbeitung

  1. customThe crude was purified via flash colurn chromatography (20% EtOAc in hexane gradient to 50% EtOAc in hexane in about 40 min.)

Quellen und Nachweise

ORD-Eintrag
ord-fd150802bc414fed9a17c531a4611b9a
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312241B2

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