Butylamine → (Z)-7,7-diethoxy-1-trimethylsilyl-3-hepten-1,5-diyne

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Reaction Steps

The diynene acetal X may be synthesized using the following procedure. Cis-1,2-dichloroethylene is reacted with 3,3-diethoxypropyne in the presence of copper iodide, palladium tetrakis(triphenylphosphine) and n-butylamine, at room temperature and in the absence of light. The product, (Z)-5-chloro-1,1-diethoxy-4-pentene-2-yne is treated with trimethylsilylacetylene in the presence of copper iodide, palladium tetrakis(triphenylphosphine), and n-butylamine at room temperature and away from light to provide (Z)-7,7-diethoxy-1-trimethylsilyl-3-hepten-1,5-diyne. The corresponding anion is then generated by treatment with an alkali metal hydroxide, such as lithium hydroxide.

Provenance & Evidence