Chlorotrimethylsilane → HCID 54544702, compound

Participants

Reaction Conditions

Reaction Steps

Methyllithium in diethyl ether (140 ml of 1.8 M solution, 0.25 mol) was added dropwise to a solution of 27.6 g (0.27 mol) of diisopropylamine in 40 ml of dry diethyl ether. The reaction mixture was cooled to -70° C. and a solution of 26.1 g (0.16 mol) of N,N-dimethylbenzeneacetamide in 75 ml of diethyl ether was added dropwise. The reaction mixture was warmed to 0° C. and 46 ml (0.36 mol) of trimethylchlorosilane were added dropwise. The reaction mixture was stirred at 25° C. overnight, the solid was filtered off, and the filtrate was distilled to give 7.65 g of β-(N,N-dimethylamino)-β-trimethylsiloxystyrene as a light yellow oil: bp 75°-78° C. (0.5 mm); 1H NMR (CDCl3) δ 2.18 ppm (s, 6H), 4.83 ppm (s, 1H), 6.7-7.6 ppm (m, 5H) and 0.04 ppm (s, 9H). Anal. Calcd. for C13H21NOSi: C, 66.33; H, 8.99; N, 5.95; Found: C, 66.47; H, 9.11; N, 5.78.

Provenance & Evidence