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Diethoxymethylsilane is used in the preparation of N,N'-methylsilanediyl-bis-phthalimide by reacting with phthalimide. It is used as a reagent in the selective reduction of carbonyl compounds, hydorosilylation of alkenes, tandem reductive aldol reaction and rhodium-catalyszed silylcarbocyclization.
Silane reducing agent; see Appendix 4. In the presence of KF or CsF, reduces aldehydes and ketones to alcohols (via the silyl ether): Tetrahedron, 37, 2165 (1981). With CsF, the reaction can be extended to esters: Synthesis, 558 (1981). Both reactions are improved in DMSO or DMF as solvent: Synthesis, 981 (1982).
Hydosilylation of olefinic compounds can be effected, e.g. in the presence of PtO2: Org. Lett., 4, 2117 (2002).
Niljianskul, N.; Zhu, S.; Buchwald, S. L. Enantioselective Synthesis of alfa-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes. Angew. Chem. 2015, 127 (5), 1658-1661.
Wang, Y. M.; Bruno, N. C.; Placeres, A. L.; Zhu, S.; Buchwald, S. L. Enantioselective Synthesis of Carbo-and Heterocycles through a CuH-Catalyzed Hydroalkylation Approach. J. Am. Chem. Soc. 2015, 137 (33), 10524-10527.
Gefahrenhinweise (EU): H225-H315-H319-H335
Highly flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.