(Z)-3-Trimethylsiloxy-2-pentene (CAS NO.: ), which is also known as Silane, [(1-ethyl-1-propenyl)oxyl]trimethyl-, (Z)-, could be produced through the following synthetic routes.

A. . In a 3-L, three-necked flask fitted with a 1-L, pressure-equalizing dropping funnel, mechanical stirrer, and efficient condenser that is connected to a nitrogen source are placed 97.5 g (1.5 mol) of zinc powder and 14.9 g (0.15 mol) of cuprous chloride. After the reaction vessel is flushed with nitrogen, a static nitrogen atmosphere is maintained for the remainder of the reaction. A mixture of 150 mL of is added to the flask, and the resulting mixture is refluxed with stirring for 30 min with the aid of an electric ing mantle. Heating is discontinued and a solution of 109 g (128 mL, 1.0 mol) of chlorotrimethylsilane and 184 g (123 mL, 1.1 mol) of in a mixture of 90 mL of ether and 350 mL of benzene is promptly added through the dropping funnel at such a rate as to maintain the reaction at gentle reflux. The addition takes about 1 hr. After the addition is complete, the mixture is heated at reflux for 1 hr and then cooled in an ice bath. While the mixture is stirred, 300 mL of aqueous 5% hydrochloric acid is added through the dropping funnel over a 10-min period. The liquid layer is decanted into a 3-L separatory funnel and the flask is washed with two 100-mL portions of ether. The ether solutions are added to the separatory funnel, the organic layer is separated, and the aqueous layer is extracted with two 200-mL portions of ether. The organic phases are combined and washed twice with 200-mL portions of saturated aqueous sodium chloride, twice with 200-mL portions of saturated aqueous sodium bicarbonate, and finally with 200 mL of saturated aqueous sodium chloride. The organic layer is dried over anhydrous magnesium sulfate, the mixture is filtered, and the filtrate is concentrated on a rotary evaporator to a volume of about 400 mL. The residual yellow liquid is distilled in a 30-cm vacuum-jacketed Vigreux column at atmospheric pressure until the boiling point is 90°C. The remaining liquid is distilled at reduced pressure to give, after a small forerun, 101–108 g (63–74%) of ethyl trimethylsilylacetate, bp 93–94°C (104 mm), nD20 1.4152–1.4154.

B. (Z)-3-Trimethylsiloxy-2-pentene. In a dry, 200-mL flask equipped with a -coated magnetic stirring bar and a three-way stopcock, one exit of which is capped with a small rubber septum, is quickly placed 1.5 g (ca. 6 mmol) of dried tetrabutylammonium fluoride hydrate. With the aid of a hypodermic syringe, 50 mL of dry tetrahydrofuran (THF) is added through the septum, and the clear solution is stirred. After 5 min, the reaction vessel is immersed in a hexane/dry ice bath, and 38.4 g (0.240 mol) of ethyl trimethylsilylacetate is added during 10 min through a syringe that is rinsed with 15 mL of dry THF. After 10 min a solution of 17.2 g (0.200 mol) of 3-pentanone  in 15 mL of dry THF is introduced during 10 min to the stirred solution with the aid of a syringe, which is then rinsed with 5 mL of dry THF. The clear solution is stirred for 3 hr, then warmed gradually to 0°C over about 1 hr and finally the temperature is held at 0°C for 2–4 hr. Meanwhile, 400 mL of pentane in a dry, nitrogen-filled, 1-L flask equipped with a drying tube and a magnetic stirring bar is cooled with stirring in a hexane/dry ice bath, and the dark-orange reaction mixture is poured into it. The reaction vessel is rinsed with three 50-mL portions of pentane. The pentane rinses are added to the reaction solution and the resulting mixture is filtered through a pad of Hyflo Super Cell on a sintered-glass filter, and the filtrate is washed with 100 mL of saturated aqueous sodium bicarbonate and 100 mL of saturated aqueous sodium chloride. The organic layer is dried over magnesium sulfate, the drying agent is remove by filtration, and the resulting solution is concentrated on a rotary evaporator at room temperature to a volume of 150 mL. The remaining liquid is distilled through a 10-cm Vigreux column. After a very small amount of forerun ( < 1 g), 21.9–24.1 g (69–76%) of 3-trimethylsiloxy-2-pentene is obtained, bp 139–142°C; n_D20 1.4133–1.4135.

Notice: Ethyl bromoacetate is intensely irritating to eyes and skin. The preparation of this ester should be carried out in an efficient hood. Caution! Benzene has been identified as a carcinogen; OSHA has issued emergency standards on its use. All procedures involving benzene should be carried out in a well-ventilated hood, and glove protection is required.