Tetrabutylammonium Fluoride → 4-(4-Chloro-phenyl)-4-methoxy-butan-1-ol
Reaktionsgleichung
C([Si]([O:18][CH2:19][CH2:20][CH2:21][CH:22]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[O:23][CH3:24])(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([CH:22]([O:23][CH3:24])[CH2:21][CH2:20][CH2:19][OH:18])=[CH:30][CH:29]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of tert-butyl-[4-(4-chloro-phenyl)-4-methoxy-butoxy]-diphenyl-silane (343 mg, 0.75 mmol) in 20 mL THF was added at room temperature TBAF (7.5 mL, 7.5 mmol, 1M in THF). The mixture was stirred for 3 h and the reaction quenched by the addition of 10 mL saturated aqueous NH4Cl. The mixture was extracted with ethyl acetate (3×15 mL) and the combined organic layers washed with brine (2×10 mL) and dried over Na2SO4. The mixture was concentrated and the product isolated by flash column chromatography eluting with 6% to 60% ethyl acetate/hexane to provide 120 mg of the title compound.