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(Iodomethyl)trimethylsilane is used for the N-alkylation of amides, in a reaction sequence to prepare unstabilized ylides for [2+3]-cycloadditions. It can react with acetoacetic acid ethyl ester to get 3-trimethylsilanyl-proπonic acid ethyl ester.
Motoo Tori.; Chiho Makino.; Kenji Hisazumi.; Masakazu Sono.; Katsuyuki Nakashima. Synthesis of a homochiral ketone having a pinguisane skeleton using phenylethylamine as a chiral auxiliary: a formal total synthesis of deoxopinguisone. Tetrahedron: Asymmetry. 2001, 12, (2), 301-307.
Dale L. Boger.; Louis R. Cerbone.; Daniel Yohannes. Oxidative coupling of methyl 6-hydroxyindole-2-carboxylate with primary amines. Preparation of 2-substituted methyl pyrrolo[2,3-e]benzoxazole-5-carboxylates. J. Org. Chem. 1988, 53, (21), 5163-5166.
Hazard Statements: H226-H315-H319-H335
Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P280g-P305+P351+P338
Wear protective gloves. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.