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

HRID 971003Notes

Reaction equation

HRID 971003 reaction equation
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]

Participants

4

Reactant 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

Product 1

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

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-0224a59bdc1a44d58a6c7b516d563460
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

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