Sodium Chloride → 1,1-Bis(methylthio)-2-(4-phenoxyphenyl)-1 butene

HRID 2372431

Reaktionsgleichung

C[Si]([CH:5]([S:8][CH3:9])[S:6][CH3:7])(C)C.CCCCCC.C([Li])CCC.[CH:21]1[CH:26]=[CH:25][C:24]([C:27]([CH2:29][CH2:30][O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=O)=[CH:23][CH:22]=1.[Cl-].[Na+]>O1CCCC1>[CH3:7][S:6][C:5]([S:8][CH3:9])=[C:25]([C:24]1[CH:23]=[CH:22][C:30]([O:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:29][CH:27]=1)[CH2:26][CH3:21]

Komponenten

Reaktionsbedingungen

Temperatur: -73 °C

Versuchsvorschrift

Trimethylsilyl-bis(methylthio)methane, 2.65 g, was dissolved in 15 ml of tetrahydrofuran and 7 ml of 1.6 mole hexane solution of n-butyl lithium was dropwise added to the solution in an argon flow under ice cooling. The mixture was stirred at the same temperature for 30 minutes. After cooling to -73° C., a solution of 2.26 g of 4-phenoxypropiophenone in 5 ml of tetrahydrofuran was dropwise added to the mixture. Then, the temperature was gradually elevated to room temperature followed by stirring for 16 hours. After saturated sodium chloride aqueous solution was added to the mixture, it was extracted with chloroform. After drying the chloroform phase over magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform : hexane =1 : 1) to give 3.04 g of the oily product.

Aufarbeitung

customwas gradually elevated to room temperature
stirringby stirring for 16 hours
extractionwas extracted with chloroform
dry with materialAfter drying the chloroform phase over magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography (chloroform : hexane =1 : 1)

Quellen und Nachweise

ORD-Eintrag: ord-3ff5bc31306346dca8e5fcacd697f3f3
Quelldatensatz: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05098928

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