反应详情

温度

-70 °C

1-Bromo-2-trimethylsilyloxyethylene (1 g, 5.3 mmol) in anhydrous ethyl ether (10 cc) is introduced under an argon atmosphere into a 50-cc round-bottomed flask. The mixture is cooled to -70° C. and a 1.2M solution (8 cc) of tert-butyllitium in pentane is then added. Stirring is performed for 90 minutes at -70° C. and then 6,10,14-trimethyl-2-pentadecanone (1.19 g) is added in solution in anhydrous ethyl ether (3 cc). The temperature is allowed to rise to about -15° C. and stirring is continued for 1 hour. The solution is cooled to -60° C. and 3N hydrochloric acid (7 cc) is then added over 15 minutes. Stirring is performed for 30 minutes at 10° C. After extracting with ether, washing the ether phases until neutral, drying the ether phases over magnesium sulphate, filtering and evaporating off the solvents, a product is obtained and is purified by flash chromatography. 3,7,11,15-Tetramethyl-2-hexadecenal (1.05 g) is thus obtained and is characterized by its infrared spectrum and its proton nuclear magnetic resonance spectrum.

1. customto rise to about -15° C.
2. stirringstirring
3. waitis continued for 1 hour
4. temperatureThe solution is cooled to -60° C.
5. stirringStirring
6. waitis performed for 30 minutes at 10° C
7. extractionAfter extracting with ether
8. washwashing the ether phases until neutral,
9. dry with materialdrying the ether phases over magnesium sulphate
10. filtrationfiltering
11. customevaporating off the solvents
12. customa product is obtained
13. customis purified by flash chromatography