Chlorotrimethylsilane → 1-Ethoxy-1,3-bis(trimethylsiloxy)hexa-1,3-diene

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Reaction Steps

Ethyl 3-oxohexanoate (20 mL, 0.13 mol) was dissolved in toluene (100 mL), and triethylamine (28 mL, 0.20 mol) and chlorotrimethylsilane (24 mL, 0.19 mol) were added thereto and stirred at room temperature for 4 hours. Hexane (200 mL) and aqueous 0.5 mol/L sodium hydrogencarbonate solution were added to the reaction mixture, and extracted three times with hexane. The organic layers were combined, and washed with aqueous saturated sodium hydrogencarbonate solution and aqueous saturated sodium chloride solution in order, then dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was dissolved in tetrahydrofuran (100 mL), and the solution was cooled to −78° C. Tetrahydrofuran solution of 2.0 mol/L lithium diisopropylamide (78 mL, 0.16 mol) was added to the resulting solution, and stirred at −78° C. for 1 hour, and then chlorotrimethylsilane (18 mL, 0.14 mol) was added thereto and further stirred at −78° C. for 8 hours. Hexane (200 mL) and water were added to the reaction mixture, and extracted three times with hexane. The organic layers were combined, and washed with aqueous 0.5 mol/L sodium hydrogencarbonate solution and aqueous saturated sodium chloride solution in order, then dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure to obtain 1-ethoxy-1,3-bis(trimethylsiloxy)hexa-1,3-diene (41 g, 100%).

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