Diethyl fumarate → Diethyl 4-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)cyclohex-4-ene-1,2-dicarboxylate

Reaktionsgleichung

[C:1]([Si:5]([O:8][C:9](=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[CH:10]=[CH2:11])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].C([Si](O/C(=C\C1C=CC(F)=CC=1)/C=C)(C)C)(C)(C)C.[C:39]([O:48][CH2:49][CH3:50])(=[O:47])/[CH:40]=[CH:41]/[C:42]([O:44][CH2:45][CH3:46])=[O:43]>>[Si:5]([O:8][C:9]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:40]([C:39]([O:48][CH2:49][CH3:50])=[O:47])[CH:41]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:11][CH:10]=1)([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:7])[CH3:6]

Komponenten

Edukt 3

HCID 638144Diethyl fumarate

HCID 21099309(Z)-tert-butyl((1-(4-fluorophenyl)buta-1,3-dien-2-yl)oxy)dimethylsilane

HCID 73742632Tert-butyl{[1-(4-fluorobenzylidene)prop-2-en-1-yl]oxy}dimethylsilane

Produkt 1

HCID 68541249Diethyl 4-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)cyclohex-4-ene-1,2-dicarboxylate

Versuchsvorschrift

To a solution of 37 g (˜80% pure, 133.1 mmol, 1 equiv.) of 1E and 1Z-tert-butyl{[1-(4-fluorobenzylidene)prop-2-en-1-yl]oxy}dimethylsilane (Example 1, step C) and 17 mL (18 g, 104.6 mmol) diethyl (2E)-but-2-enedioate in 200 mL xylenes under nitrogen atmosphere was heated at 160° C. for 5 hr then cooled to RT. The solvent was evaporated under vacuum to give an oil which was used without further purification.