(4-Iodobut-3-en-2-yl)(trimethyl)silane

synthetischethe first reported preparation of this reagent lacked full experimental details. The preparation given is a compilation of thework of several groups; the various steps have been selected to give optimum yields. 2-Propyn-1-ol is converted3 into its 3-(trimethylsilyl) derivative (1), which is then reduced4 using sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al). The intermediate vinylaluminum is reacted with iodine to produce the (Z)-iodoalkene (2). Treatment of this with lithium dimethylcuprate gives the allylic alcohol (3);. transformation into (E)-(3-chloro-1-methyl-1-propenyl)trimethylsilane (4) followed by halogen exchange with sodium iodide then gives reagent (5).