反应详情

3,4-Dihydroisoquinoline (1.31 g, 10.0 mmol) was dissolved in 3 ml MeOH in a 3-neck 25 ml round bottom flask fitted with a condenser, drying tube and stirrer bar, and cooled in an ice bath. n-Octyl p-toluenesulfonate (2.84g, 10.0 mmol)*, dissolved in 7.0 ml methanol, was added dropwise over about 7 minutes via an addition funnel. The ice bath was removed and replaced with an oil bath and the colorless clear solution heated to reflux for at least 8 hours during which time the reaction solution turned yellow. Removal of the methanol in vacuo gave slightly colored solid product which was triturated with about 7.5 ml acetone. The acetone insoluble solids were filtered, washed with more acetone and dried in a vacuum desiccator. Yield of colorless solids was 1.91 g. A second batch of solids was recovered from the acetone filtrate/washing and filtered, washed with acetone and dried to give 0.31 gm colorless solids.

1. customfitted with a condenser
2. customdrying tube and stirrer bar
3. temperaturecooled in an ice bath
4. additionwas added dropwise over about 7 minutes via an addition funnel
5. customThe ice bath was removed
6. customreplaced with an oil bath
7. temperaturethe colorless clear solution heated
8. temperatureto reflux for at least 8 hours during which time the reaction solution
9. customRemoval of the methanol in vacuo
10. customgave slightly colored solid product which
11. customwas triturated with about 7.5 ml acetone
12. filtrationThe acetone insoluble solids were filtered
13. washwashed with more acetone
14. customdried in a vacuum desiccator
15. customA second batch of solids was recovered from the acetone filtrate/washing
16. filtrationfiltered
17. washwashed with acetone
18. customdried