反应详情

4-Trimethylsilyloxycyclohexylacetylene (20 mmol) was dissolved in THF (20 ml), followed by dropwise adding a n-butyllithium-hexane solution (1.61M, 12.4 ml) while stirring the above solution under ice cooling, stirring the reaction solution under ice cooling for 30 minutes, dropwise adding a solution of 2-(4-pentylcyclohexyl)acetaldehyde (4.0 g) in THF (10 ml), raising the temperature of the reaction solution up to room temperature after completion of the dropwise addition, stirring it for 5 hours, adding dilute hydrochloric acid (5 ml) to the resulting raw solution, extracting the mixture with ethyl acetate (150 ml), washing the organic phase with water, drying over anhydrous MgSO4, concentrating under reduced pressure to obtain a brown oil, which is recrystallized from a mixed solution of ethyl acetate-heptane, to obtain 1-(4-trimethylsilyloxycyclohexyl)-4-(4-pentylcyclohexyl)-1-butyn-3-ol (5.0 g) (white crystal).

1. additionby dropwise adding a n-butyllithium-hexane solution (1.61M, 12.4 ml)
2. stirringstirring the reaction solution under ice cooling for 30 minutes
3. additionafter completion of the dropwise addition
4. stirringstirring it for 5 hours
5. extractionextracting the mixture with ethyl acetate (150 ml)
6. washwashing the organic phase with water
7. dry with materialdrying over anhydrous MgSO4
8. concentrationconcentrating under reduced pressure
9. customto obtain a brown oil, which
10. customis recrystallized from a mixed solution of ethyl acetate-heptane