A. tert-Butyl(but-3-ynyloxy)diphenylsilane. A dry, 250-mL, round-bottomed flask is fitted with a rubber septum and a magnetic stirring bar. The flask is charged with 3-butyn-1-ol (2.1 g, 30 mmol) (Note 1) and dry dichloromethane (60 mL) (Note 2). After addition of 8.5 g (31 mmol) of tert-butyldiphenylchlorosilane (Note 3), the reaction flask is immersed in a water bath and imidazole (2.86 g, 42 mmol) is added in one portion followed by 4-dimethylaminopyridine (0.37 g, 3 mmol). The water bath is removed and the reaction mixture is stirred at room temperature overnight. The white precipitate is filtered through a sintered glass funnel (`M' frit). The precipitate is washed with cold dichloromethane (50 mL). The combined filtrates are transferred to a 500-mL separatory funnel and washed with 1 M aqueous hydrochloric acid solution (50 mL) and water (100 mL), successively. The organic layer is dried over magnesium sulfate and concentrated by rotary evaporator. Bulb-to-bulb distillation of the residue (bp 150–152°C/1 mm) gives 8.90 g (96%) of tert-butyl(but-3-ynyloxy)diphenylsilane as a colorless oil (Note 4).

B. 1-[(tert-Butyldiphenylsilyloxy)]-dec-3-en-5-ol. A flame-dried, 250-mL, round-bottomed flask equipped with a gas inlet stopcock (Figure 1) is fitted with a rubber septum and a magnetic stirring bar, and flushed with nitrogen. The flask is charged with tert-butyl(but-3-ynyloxy)diphenylsilane (5.55 g, 18 mmol) and dry dichloromethane (60 mL), immersed in a cold water bath and stirred. Within 20 min, 5.10 g (19.8 mmol) of zirconocene hydrochloride (Note 5) is added in five portions. The water bath is removed and the reaction mixture is stirred at room temperature until a homogenous solution forms. The resulting golden-yellow solution is stirred for another 20 min (Note 6) and then cooled to −60°C. By syringe, dimethylzinc (2.0 M solution in toluene, 10.4 mL, 20.8 mmol) (Note 1) is added dropwise over 45 min while the bath temperature is kept at −60°C. The resulting orange-yellow solution is stirred for an additional 10 min at −60°C after the addition is completed. The reaction flask is immersed in an ice bath, and a solution of 2.16 g (21.6 mmol) of hexanal (Note 1) in dry dichloromethane (10 mL) is added via syringe over 45 min. The reaction mixture is stirred at 0°C for another 6 hr. The yellow solution is poured slowly into a beaker containing ice-cold aqueous 5% sodium bicarbonate solution (200 mL) and vigorous stirring is continued at room temperature until gas evolution subsides. The mixture is transferred to a 1-L separatory funnel and is extracted with diethyl ether (3 × 200 mL) (Note 7). The combined extracts are washed with a saturated aqueous sodium chloride solution (300 mL) and dried over sodium sulfate. The cloudy solution is filtered through a pad of Florisil (Note 8) loaded on a sintered glass funnel (`M' frit). The clear filtrate solution is concentrated by rotary evaporator. The residue is layered on a column of silica gel (150 g, column diameter: 6.0 cm) and eluted (ethyl acetate/hexane, 1:30 to 1:15 as eluents) to give 4.90 g (66%) of 1-[(tert-butyldiphenyl-silyl)oxy]-dec-3-en-5-ol as a colorless oil (Note 9).