Chemical Properties
Clear colorless liquid
Physical properties
bp 35 °C/15 mmHg; d 0.858 g cm?3.
Uses
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.
Uses
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.
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.]
