反应详情

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%).

1. extractionextracted three times with hexane
2. washwashed with aqueous saturated sodium hydrogencarbonate solution and aqueous saturated sodium chloride solution in order
3. dry with materialdried over anhydrous sodium sulfate
4. customthe solvent was evaporated away under reduced pressure
5. dissolutionThe resulting residue was dissolved in tetrahydrofuran (100 mL)
6. temperaturethe solution was cooled to −78° C
7. stirringstirred at −78° C. for 1 hour
8. stirringfurther stirred at −78° C. for 8 hours
9. extractionextracted three times with hexane
10. washwashed with aqueous 0.5 mol/L sodium hydrogencarbonate solution and aqueous saturated sodium chloride solution in order
11. dry with materialdried over anhydrous sodium sulfate
12. customthe solvent was evaporated away under reduced pressure