Chlorotrimethylsilane → 3-Methyl-8-(trimethylsilyl)-5,6,7,8-tetrahydroquinoline

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Reaction Steps

A mixture of 5,6,7,8-tetrahydro-3-methylquinoline (29.4 g, 0.2 M) and tetrahydrofuran (THF) (50 ml) was added to a mixture of a 1.55 molar solution of butyl lithium in hexane (129 ml, 0.2 M) and THF (50 ml), maintained below 10°. After 0.5 hour the mixture was blown over by inert gas onto a mixture of trimethylsilyl chloride (50 ml, 0.4 M) in the THF (100 ml), maintained below 10°. After 0.5 hour, the mixture was evaporated and the residue extracted with hexane. The hexane extracts were evaporated with the residue distilled to give the title compound (40 g, 91%) b.p. 118°-124°/5 mbar. (Found: C70.9; H,9.65; N,6.4% C13H21NSi requires: C,71.2; H,9.6; N6.4%).

Provenance & Evidence