反应详情

温度

-70 °C

Diisopropylamine (2.4 g, 23.8 mmole) was dissolved in anhydrous tetrahydrofuran (50 ml) under argon, and the solution was cooled at -70° C. 1.6M n-butyllithium-hexane solution (14.8 ml, 23.7 mmole) was added dropwise to the solution, followed by stirring at -70° C. for 10 minutes. Tetrahydrofuran (10 ml) solution containing ethyl phenylacetate (3.24 g, 20 mmole) was added, while maintaining the reaction solution at not higher than -60° C. After stirring was continued for 30 minutes under the same conditions, a solution of 4-acetoxypentyl iodide (4.8 g, 20 mmole) in hexamethylphosphortriamide (4 ml) was added dropwise to the reaction solution. Following the dropwise addition, stirring was continued at -70° C. for another 1 hour, and the reaction temperature was allowed to rise to room temperature. 2N hydrochloric acid (30 ml) was added, and the product was extracted with isopropyl ether. The organic layer was washed with water, dried and concentrated under reduced pressure. The residue was chromatographed on silica gel, and development was effected with isopropyl ether:hexane (1:1) to yield ethyl 6-acetoxy-2-phenylhexanoate (5 g, 90%).

1. addition1.6M n-butyllithium-hexane solution (14.8 ml, 23.7 mmole) was added dropwise to the solution
2. additionwas added
3. temperaturewhile maintaining the reaction solution at not higher than -60° C
4. stirringAfter stirring
5. waitwas continued for 30 minutes under the same conditions
6. additionthe dropwise addition
7. stirringstirring
8. waitwas continued at -70° C. for another 1 hour
9. customto rise to room temperature
10. extractionthe product was extracted with isopropyl ether
11. washThe organic layer was washed with water
12. customdried
13. concentrationconcentrated under reduced pressure
14. customThe residue was chromatographed on silica gel, and development