反应详情

To 150 ml of a mixture of tetrahydrofuran-diglyme (2:15) were added 12 g of 1-phenyl-8-(2-tetrahydropyranyloxy)-1-octyne and 3.35 g of lithium aluminum hydride. The mixture was heated and tetrahydrofuran was distilled off until the inner temperature became 120° C. After heating under reflux at the same temperature for 1 hour, the mixture was ice-cooled. Ice was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% hydrochloric acid, water, sodium hydrogen carbonate solution, saline water in the order mentioned, dried, and then the solvent was distilled off. The residue was dissolved in 250 ml of methanol and 1.1 g of p-toluenesulfonic acid was added thereto. The mixture was stirred at room temperature for 1 hour and 2 ml of triethylamine was added to the mixture. Methanol was distilled off and the residue was purified by silica gel column chromatorgraphy (solvent: hexane-ethyl acetate=3:1) to give 7.5 g of (E)-8-phenyl-7-octen- 1-ol as an oily substance.

1. temperatureThe mixture was heated
2. distillationtetrahydrofuran was distilled off until the inner temperature
3. custombecame 120° C
4. temperatureAfter heating
5. temperatureunder reflux at the same temperature for 1 hour
6. temperaturecooled
7. additionIce was added to the mixture
8. extractionthe mixture was extracted with ethyl acetate
9. washThe organic layer was washed with 10% hydrochloric acid, water, sodium hydrogen carbonate solution, saline water in the order
10. customdried
11. distillationthe solvent was distilled off
12. dissolutionThe residue was dissolved in 250 ml of methanol
13. addition1.1 g of p-toluenesulfonic acid was added
14. addition2 ml of triethylamine was added to the mixture
15. distillationMethanol was distilled off
16. customthe residue was purified by silica gel column chromatorgraphy (solvent: hexane-ethyl acetate=3:1)