Iodine → (S,E)-tert-Butyl(1-iodo-5-phenylpent-1-en-3-yloxy)dimethylsilane

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Reaction Steps

A flame dried Schlenk flask, evacuated and purged with nitrogen, was charged with alkyne 88 (1.50 g, 5.46 mmol, 1 eq.). Anhydrous CH2Cl2 (35 ml) was added and the reaction stirred at r.t. Zr(Cp)2HCl (2.82 g, 10.9 mmol, 2 eq.) was added as a solid, in portions. The yellow suspension was stirred at r.t. for 1 h. The resulting yellow solution was cooled to 0° C. and iodine (1.52 g, 6.01 mmol, 1.1 eq.) added as a solid, in one portion. The cooling bath was removed and the reaction mixture stirred at room temperature for 1 h. The reaction mixture was poured into water (100 ml) and extracted with 40/60 petroleum ether (4×50 ml). The combined organic phases were washed with water (100 ml), saturated Na2S2O3 solution (2×100 ml) and brine (100 ml) before being dried (MgSO4), filtered, and concentrated to give the crude material. This was purified by flash chromatography, eluting with 40/60 petroleum ether. The fractions containing product were combined and washed with saturated Na2S2O3 solution (20 ml), dried (MgSO4), filtered, and concentrated to give the title compound 89 (1.98 g, 90%) as a clear, colourless oil. Analytical data consistent with the literature (Sato, F. et al., EP 1211241 A1, Taisho Pharmaceutical co., LTD (2002)).

Provenance & Evidence