Methyl 2-Trimethylsilylacrylate

Abstract

[18269-31-3] C7H14O2Si (MW 158.30) InChI = 1S/C7H14O2Si/c1-6(7(8)9-2)10(3,4)5/h1H2,2-5H3 InChIKey = XYEVJASMLWYHGL-UHFFFAOYSA-N (reactive, α-silyl Michael acceptor for conjugate addition of carbanions, enolate anions, organolithium reagents, and Grignard reagents; affords 3-cyclopentenecarboxylates and cyclohexanecarboxylates by [3 + 2] and [4 + 2] annulation methods; provides α-silyl esters and vinylsilanes by organolithium conjugate additions1, 3, 5) Physical Data: bp 75 °C/50 mmHg, 152 °C/690 mmHg. Solubility: sol Et2O, THF, EtOH, and most organic solvents. Analysis of Reagent Purity: IR, NMR, GC. Preparative Methods: prepared2a,b by the reaction of (E)-2-(Trimethylsilyl)vinyllithium with Methyl Chloroformate or by carbonation of the corresponding Grignard reagent prepared from (1-Bromovinyl)trimethylsilane,2c giving 2-trimethylsilylacrylic acid. The methyl ester is prepared from the acid by direct esterification with absolute methanol in the presence of mineral acid, by reaction with Diazomethane at low temperature, or by treatment with BF3ċMeOH complex. For preparation of various trialkylsilylacrylic acid esters2d and t-butyl 2-trimethylsilylcrotonate,8 see the cited references. Handling, Storage, and Precautions: should be stored in a refrigerator and addition of a few crystals of ionol is recommended in order to prevent polymerization. Use in a fume hood.