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

HRID 2378211노트

반응식

HRID 2378211 반응식
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]

참가 물질

4

반응물 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

생성물 1

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

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-fcd48dd720544815a41b6af75f4e62dc
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07470723B2

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