Uses
2-Ethoxycarbonylallyltrimethylsilane is used for 2-ethoxycarbonylallylation of aldehydes and acetals; the allylation products are useful precursors to α-
methylene-γ-butyrolactones; precursor of allyl cation equivalents for [3 + 2] and [3 + 4] cycloadditions.
Preparation
Preparative Methods of 2-Ethoxycarbonylallyltrimethylsilane: a three-step synthesis from Diethyl Malonate has been reported. t-Butyl and
trimethylsilyl esters are also prepared by this method. Syntheses from ethyl diethylphosphonoacetate and
ethyl α-bromoacrylate also have been reported, but the simplest procedure involves the reaction of
ethoxalyl chloride with two equivalents of Trimethylsilylmethylmagnesium Chloride followed by
treatment with Thionyl Chloride (53% yield). The CeIII-mediated reaction of
trimethylsilylmethylmagnesium chloride with Diethyl Oxalate is also reported to give 2-
ethoxycarbonylallyltrimethylsilane in 45% yield.
storage
2-Ethoxycarbonylallyltrimethylsilane can be stored in a glass bottle.
