1-(Cyanomethyl)-3,5-dimethoxybenzene → (3,4-Dimethoxyphenyl)(3,5-dimethoxyphenyl)methanone

HRID 366605

Reaktionsgleichung

Reaktionsgleichung von HRID 366605
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1OC)[C:6](C1C=CN=CC=1)=[O:7].C([Li])CCC.Br[C:25]1[CH:26]=[C:27]([O:33][CH3:34])[C:28]([O:31][CH3:32])=[CH:29][CH:30]=1.[CH3:35][O:36]C1C=C(C=C(OC)C=1)C#N>>[CH3:34][O:33][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][C:28]=1[O:31][CH3:32])[C:6]([C:5]1[CH:14]=[C:15]([O:36][CH3:35])[CH:16]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:7]

Komponenten

5

Edukt 4

HCID 294821-(Cyanomethyl)-3,5-dimethoxybenzeneHCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 215846084-(3,4-Dimethoxybenzoyl)pyridineHCID 178418339Butyllithium

Produkt 1

HCID 21584591(3,4-Dimethoxyphenyl)(3,5-dimethoxyphenyl)methanone

Versuchsvorschrift

3,4,3',5'-Tetramethoxybenzophenone was prepared analogously to 4-(3,4-dimethoxybenzoyl)pyridine using butyl lithium (9 mL, 22 mmol, 2.5M), 4-bromoveratrole (2.9 mL, 20 mmol) and 3,5-dimethoxybenzonitrile (3.75 g, 23 mmol). The crude product was purified by flash column chromatography (silica gel, methylene chloride) to afford 1.54 g (26%) of the product: mp 107-110° C.; 1H NMR (CDCl3) δ 7.53-7.39 (m, 2 H), 6.95-6.84 (m, 3 H), 6.70-6.60 (m, 1 H), 3.96 (s, 3 H), 3.95 (s, 3 H), 3.83 (s, 6 H); 13C NMR (CDCl3) δ 195.0, 160.4, 153.0, 148.9, 140.1, 130.0, 125.4, 112.0, 109.7, 107.5, 104.1, 56.0, 55.5; Anal. Calcd for C17H18O5. Theoretical: C, 67.54; H, 6.00. Found: C, 67.38; H, 5.96.

Aufarbeitung

  1. customThe crude product was purified by flash column chromatography (silica gel, methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-8e2b16d3978447308d86c87c0e8071ae
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130226

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