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Ethyl trimethylsilylacetate is used in the synthesis of ethyl-2,2-dibromo-2-(trimethylsilyl)acetate. It was also used to silylate the enolizable aldehydes and ketones.
Thomas Poisson.; Vincent Gembus.; Sylvain Oudeyer.; Francis Marsais.; Vincent Levacher. Product-Catalyzed Addition of Alkyl Nitriles to Unactivated Imines Promoted by Sodium Aryloxide/Ethyl(trimethylsilyl)acetate (ETSA) Combination. J. Org. Chem. 2009, 74, (9), 3516-3519.
O. W. Webster.; W. R. Hertler.; D. Y. Sogah.; W. B. Farnham.; T. V. RajanBabu. Group-transfer polymerization. 1. A new concept for addition polymerization with organosilicon initiators. J. Am. Chem. Soc. 1983, 105, (17), 5706-5708.
Reagent for silylation, under nucleophilic catalysis by TBAF, particularly of sensitive substrates, since the by-product (ethyl acetate) is neutral and filtration is avoided: J. Am. Chem. Soc., 98, 2346 (1976). Alcohols, phenols, ketones, thiols, carboxylic acids and terminal alkynes can be silylated: Bull. Chem. Soc. Jpn., 54, 805 (1981). For conversion of ketones to silyl enol ethers, see: Org. Synth. Coll., 7, 512 (1990).
Aromatic aldehydes undergo F- promoted Reformatsky-like addition: Tetrahedron Lett., 1699 (1976). Further heating results in Peterson-type elimination to give the ɑß-unsaturated ester: J. Org. Chem., 60, 6582 (1995):
Grignard reagents give tertiary carbinols which give 1,1-disubstituted ethylenes by Peterson elimination: Tetrahedron Lett., 23, 1035 (1982). See Appendix 4.
Hazard Statements: H226
Flammable liquid and vapour.
Precautionary Statements: P210-P280a-P240-P241-P303+P361+P353-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Dispose of contents/container in accordance with local/regional/national/international regulations.