Tetrahydrofuran → Octadecyl vinyl methylchlorosilane

関与物質

反応手順

(Me2N--SiMeC18H37)--CH2CH2 --(C8H17 --SiMe--NMe2) was prepared as follows. Dichloro-methylvinylsilane (92 grams, 0.8 moles, from the Aldrich Chemical Co., Milwaukee, Wis., USA) and 250 mL of tetrahydrofaran (THF) were added to a reaction flask. A 1M solution of octadecylmagnesium chloride (800 mL) in THF (from Aldrich Chemical Co.) was added portionwise over about 1.5 hours with stirring and cooling to 0° to 10°. The resulting dark mixture warmed to 26° during the next 30 minutes. Hexane was added (2 L), and the resulting solid was filtered off. The volatiles were removed from the filtrate on a rotary evaporator, and hexane was added to the residue. The solid was filtered off, and the volatiles removed from the filtrate again to yield an oil. Thionyl chloride (12 mL) was added to the oil to convert any silanol to chlorosilane. This solution was heated to 45° and allowed to stand overnight at ambient temperature. After removal of volatiles, the resulting black mixture was vacuum distilled, providing a 134-g fraction of octadecyl vinyl methylchlorosilane (compound A), as a clear, colorless oil with a boiling point of 170°-183°/0.1 mm. Gas chromatography/mass spectrometry (GC/MS) showed the product to be 87% octadecyl vinyl methylchlorosilane and 10% octadecyl chloride.

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