Lithium Hexamethyldisilazide → 4-[1-(3,5-Dimethoxyphenyl)prop-1-enyl]-1,2-dimethoxybenzene

HRID 971026

Reaktionsgleichung

Reaktionsgleichung von HRID 971026
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=2)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CO[C:35]1C=C(C(C2C=CC=C(OC)C=2)=CC#N)C=C(OC)[CH:40]=1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[CH3:22][O:21][C:15]1[CH:14]=[C:13]([C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:35][CH3:40])[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=1

Komponenten

5

Edukt 3

HCID 2733832Lithium HexamethyldisilazideHCID 21584591(3,4-Dimethoxyphenyl)(3,5-dimethoxyphenyl)methanoneHCID 692052993-(3,5-Dimethoxy-phenyl)-3-(3-methoxy-phenyl)-acrylonitrile

Produkt 1

HCID 692026294-[1-(3,5-Dimethoxyphenyl)prop-1-enyl]-1,2-dimethoxybenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Katalysator

Versuchsvorschrift

(3,4-dimethoxyphenyl)-(3,5-dimethoxyphenyl)methanone (0.96 g, 3.18 mmol), (ethyl)triphenylphosphonium bromide (2.36 g, 6.35 mmol), and lithium bis(trimethylsilyl)amide (1.0 M solution in THF, 6.35 ml, 6.35 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 column chromatography (10% EtOAc in hexane gradient to 20% EtOAc in hexane in about 30 min.) to give 4-[1-(3,5-dimethoxyphenyl)prop-1-enyl]-1,2-dimethoxybenzene a light brown oil (0.97 g, 97%): 1HNMR (CDCl3) δ 6.89-6.83 (m, 2H, Ar), 6.76-6.68 (m, 4H, Ar), 6.43-6.39 (m, 3H, Ar), 6.36-6.34 (m, 3H, Ar), 6.20-6.03 (m, 2H, double bond protons), 3.91 (s, 3H, OCH3), 3.86 (s, 3H, OCH3), 3.83 (s, 6H, 2OCH3), 3.78 (s, 6H, 2OCH3), 3.74 (s, 6H, 2OCH3), 1.78-1.74 (m, 6H, 2CH3): 13C NMR (CDCl3) δ 160.7, 160.6, 148.7, 148.7, 148.3, 148.0, 145.4, 142.3, 142.3, 142.2, 135.6, 132.5, 124.4, 122.8, 122.6, 119.9, 113.3, 111.0, 110.9, 110.3, 108.2, 105.8, 99.2, 99.0, 56.0, 56.0, 55.5, 55.4, 15.9, 15.8. Anal. Calcd. For C19H22O4: C, 72.59; H, 7.05. Found: C, 72.43; H, 6.96.

Aufarbeitung

  1. customThe crude was purified via flash column chromatography (10% EtOAc in hexane gradient to 20% EtOAc in hexane in about 30 min.)

Quellen und Nachweise

ORD-Eintrag
ord-8ce98792a24d46f0a7f0e28cb2259ea7
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312241B2

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