METHYL (1-TRIMETHYLSILYL)ACRYLATE

Physical properties

bp 75 °C/50 mmHg, 152 °C/690 mmHg.

The Uses of METHYL (1-TRIMETHYLSILYL)ACRYLATE

Methyl 2-Trimethylsilylacrylate is widely used as 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 additions.

Preparation

Methyl 2-Trimethylsilylacrylate is prepared by the reaction of (E)-2- (trimethylsilyl)vinyllithium with methyl chloroformate or by carbonation of the corresponding Grignard reagent prepared from (1-bromovinyl)trimethylsilane, 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 BF3·MeOH complex.