Lithium Hexamethyldisilazide → 3-(3-Methoxy-4-nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-acrylonitrile

HRID 971003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 971003
COC1C=CC(C(C2C=CC(OC)=C(OC)C=2)=[CH:10][C:11]#[N:12])=CC=1[N+]([O-])=O.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([C:37]([C:39]2[CH:44]=[C:43]([O:45][CH3:46])[C:42]([O:47][CH3:48])=[C:41]([O:49][CH3:50])[CH:40]=2)=O)[CH:31]=[CH:32][C:33]=1[N+:34]([O-:36])=[O:35].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>>[CH3:26][O:27][C:28]1[CH:29]=[C:30]([C:37]([C:39]2[CH:44]=[C:43]([O:45][CH3:46])[C:42]([O:47][CH3:48])=[C:41]([O:49][CH3:50])[CH:40]=2)=[CH:10][C:11]#[N:12])[CH:31]=[CH:32][C:33]=1[N+:34]([O-:36])=[O:35]

Komponenten

4

Edukt 3

HCID 2733832Lithium HexamethyldisilazideHCID 69205076(3-Methoxy-4-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanoneHCID 692056143-(4-Methoxy-3-nitro-phenyl)-3-(3,4-dimethoxy-phenyl)-acrylonitrile

Produkt 1

HCID 692040173-(3-Methoxy-4-nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-acrylonitrileAusbeute 70 %

Versuchsvorschrift

3-(3-Methoxy-4-nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-acrylonitrile (E and Z isomers) were prepared analogously to 3-(4-methoxy-3-nitro-phenyl)-3-(3,4-dimethoxy-phenyl)-acrylonitrile using (3-methoxy-4-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone (1.2 g, 3.5 mmol), lithium bis(trimethylsilyl)amide (3.9 ml, 3.9 mmol) and diethyl cyanomethylphosphate (0.7 g, 3.9 mmol). The crude product was purified by flash chromatography (silica gel, CH2Cl2) to afford mixture isomers of 3-(3-methoxy-4-nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-acrylonitrile (0.9 g, 70%): 1H NMR (CDCl3) δ 7.93 (dd, J=8.4 and 6 Hz, 1H), 7.06-6.96 (m, 2H), 6.65 (s, 1H), 6.46 (s, 2H), 5.80(5.71) (s, 1H), 4.00-3.81 (m, 12H).

Aufarbeitung

  1. customThe crude product was purified by flash chromatography (silica gel, CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-0224a59bdc1a44d58a6c7b516d563460
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312241B2

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