DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL

Chemical properties

Clear colorless liquid

Physical properties

bp 35 °C/15 mmHg; d 0.858 g cm?3.

The Uses of DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL

1-Methoxy-2-methyl-1-(trimethylsilyloxy) propene is widely used as functional equivalent of enolate of methyl isobutyrate; ester enolate surrogate in electrophilic reactions including alkylation, aldol reaction, Michael reaction, initiator for group transfer polymerization of acrylates, nitroarylation, oxidation, dimerization, and cycloadditions.

The Uses of DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL

1-Methoxy-2-methyl-1-(trimethylsiloxy)propene is used in the synthesis of chiral β-lactams by reacting with (S)-alkylidene(1-arylethyl)amines in the presence of titanium tetrachloride. It acts as a catalyst or initiator in the group-transfer polymerization. It is also used as a versatile reagent in conjugate addition4 and aldol reactions.

What are the applications of Application

Methyl trimethylsilyl dimethylketene acetal is Methyl trimethylsilyl dimethylketene acetal has been used: ? in the synthesis of chiral β-lactams by reacting with (S)-alkylidene(1-arylethyl)amines in the presence of titanium tetrachloride ? as a catalyst or initiator in the group-transfer polymerization ? as a versatile reagent in conjugate addition and aldol reactions.

Preparation

The title compound is a prototypical ketene silyl acetal (KSA) that can been prepared by either of the two most commonly employed methods: (a) deprotonation of the |á-hydrogen of an ester followed by silylation (1),16 and (b) metal-catalyzed hydrosilylation of |á,|?-unsaturated esters(2).

Purification Methods

Add Et2O, wash with cold H2O, dry (Na2SO4), filter, evaporate Et2O, and distil the oily residue in a vacuum. [Ainsworth et al. J Organometal Chem 46 59 1972.]