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(Chloromethyl)trimethylsilane is used for Wittig reaction and building blocks.
Akira Sekiguchi; Wataru Ando. Direct synthesis of terminal olefins from ketones. Application of (chloromethyl)trimethylsilane to a Wittig reaction. J. Org. Chem. 1979, 44 (3), 413-415.
John W. Connolly; Grant Urry. The Wurtz Reaction of Chloromethyltrimethylsilane. A Classical Study. J. Org. Chem. 1964, 29 (3), 619-623.
Treatment with s-BuLi at -78o gives ɑ-lithio-ɑ-chloromethyltrimethylsilane which reacts with aldehydes and ketones to give ɑß-epoxy silanes, readily hydrolyzed to homologated aldehydes: Tetrahedron, 39, 867 (1983):
Metallation gives useful precursors of various organosilicon compounds. For use of the Grignard in the olefination of ketones, see: J. Org. Chem., 39, 3264 (1974); 52, 281 (1987). For Ni-catalyzed reaction of the Grignard with allylic dithioacetals, see: J. Org. Chem., 53, 5582 (1988); Org. Synth. Coll., 9, 727 (1998); for an example with reaction scheme, see trans-Cinnamaldehyde, A14689.
For a review of the chemistry of chloromethyltrimethylsilane, see: Synthesis, 717 (1985).
Gefahrenhinweise (EU): H225-H315-H319-H335
Highly flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
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