反应详情

温度

0 °C

In a second stage, the dianion of propargyl alcohol is formed by adding 19 g of propargyl alcohol, with stirring, to the above reaction mixture, cooled to 0° C. At the end of the addition, the mixture is stirred for another 1 h 30 min at ambient temperature. 0.5 g of copper cyanide is then added and stirring is continued for another 1 h 30 min, still at ambient temperature. 40.54 g of 1-chloro-2,5-tetradecadiyne are introduced dropwise into the mixture thus obtained, cooled to 0° C. The mixture is left to stand overnight at ambient temperature and it is then heated under reflux for 9 hours. The solvent is then removed by evaporation under vacuum and the residue obtained is extracted with methylene chloride. The organic phase is then washed with water, dried over magnesium sulphate and concentrated under reduced pressure. The solid obtained is dissolved in 350 cm3 of boiling hexane. The expected alcohol crystallizes on cooling. It is filtered off and dried. 25 g of 2,5,8-heptadecatriyn-1-ol are obtained in the form of white crystals whose melting point is 48° C. Its 1H NMR spectrum is consistent with the expected structure.

1. additionAt the end of the addition
2. stirringthe mixture is stirred for another 1 h 30 min at ambient temperature
3. stirringstirring
4. customthus obtained
5. temperaturecooled to 0° C
6. waitThe mixture is left
7. waitto stand overnight at ambient temperature
8. temperatureit is then heated
9. temperatureunder reflux for 9 hours
10. customThe solvent is then removed by evaporation under vacuum
11. customthe residue obtained
12. extractionis extracted with methylene chloride
13. washThe organic phase is then washed with water
14. dry with materialdried over magnesium sulphate
15. concentrationconcentrated under reduced pressure
16. customThe solid obtained
17. customThe expected alcohol crystallizes
18. temperatureon cooling
19. filtrationIt is filtered off
20. customdried