Allylchlorodimethylsilane → Allyldimethyl-[4-(terahydropyran-2-yloxy)-but-1-ynyl]-silane

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A solution of n-butyllithium (12.0 ml, 30 mmol, 2.5 mol dm−3 in hexanes) was added dropwise to a stirred, cooled (−78° C.) solution of compound 2 (4.62 g, 30 mmol) in THF (60 ml) under an atmosphere of dry nitrogen. The reaction mixture was maintained at −78° C. for 1.5 h and a solution of allylchlorodimethylsilane (4.04 g, 30 mmol) in THF (20 ml) added dropwise. The reaction mixture was allowed to warm to room temperature, washed with water and the organic layer extracted into ethyl acetate/hexane (3 times). The combined extracts were washed with brine, dried (MgSO4) and the solvent removed in vacuo to yield a clear oil. The crude product was purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1), Rf: 0.48]

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