Chlorotrimethylsilane → Trimethyl[(thiophen-2-yl)methyl]silane

Reaktionsgleichung

[Li]CCCC.[C:6]1([S:12][CH3:13])[CH:11]=[CH:10]C=C[CH:7]=1.Cl[Si:15]([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[S:12]1[CH:13]=[CH:10][CH:11]=[C:6]1[CH2:7][Si:15]([CH3:18])([CH3:17])[CH3:16]

Komponenten

Versuchsvorschrift

To a stirred solution of 143 mL of 1.4M n-BuLi (0.20 mol) in 55 mL of dry THF, was added dropwise at room temperature under a nitrogen atmosphere 24.8 g (0.20 mol) of thioanisole. Upon completion of the addition, the yellow mixture began to reflux spontaneously. The mixture was stirred at room temperature for 3 hours. Upon addition of 21.84 g (0.20 mol) of chlorotrimethylsilane, the mixture again began to reflux spontaneously. After stirring at room temperature overnight, the mixture was quenched with 100 mL of 5% of HCl. The aqueous layer was separated, and the organic layer was dried over MgSO4, filtered, and the solvent removed in vacuo from a water bath at 45° C. The crude product was distilled to give 19.22 g (49%) of the colorless sulfide, bp 84°-86° C./0.3 Torr; 1H NMR (CDCl3) δ0.17 (s, 9H, Si(CH3)3), 2.13 (s, 2H, CH2S), 7.0-7.42 (m, 5H, phenyl).