Ethyl 2-(Methyldiphenylsilyl)propanoate

The Uses of Ethyl 2-(Methyldiphenylsilyl)propanoate

Precursor to 1,1-disubstituted 1-propenes; reacts with primary Grignard reagents to give 2-(methyldiphenylsilyl)-3- alkanones, which in turn lead to regioselectively derived methyldiphenylsilyl enol ethers or to 3-alkanones; reagent for the synthesis of α-methyl-α,β-unsaturated esters.

Preparation

whereas the direct silylation of the lithium enolate of an ester normally results in the formation of a mixture of the α-silyl ester and the corresponding silyl ketene acetal, the reaction of lithium ester enolates with methyldiphenylchlorosilane gives exclusively the α-methyldiphenylsilyl ester. This direct C-silylation is the best general route to α-silyl esters.