반응 #2300179

반응 방정식

Benzyl bromide

4-(4-fluorophenyl)pyridine

sodium borohydride

→

title compound

수율 78.2%

4-(4-Fluorophenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)pyridine

수율 78.2%

용매

acetone

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도under reflux for 3 days
3. 3
   기타the solid was collected
4. 4
   세척washed with acetone and diethyl ether
5. 5
   기타dried in vacuo
6. 6
   workup.DISSOLUTIONThe solid was dissolved in methanol (400 mL)
7. 7
   온도water (100 mL), cooled to 0° C.
8. 8
   온도heated
9. 9
   온도under reflux for 18 hours
10. 10
    온도The mixture was cooled
11. 11
    기타the solvent was evaporated under reduced pressure
12. 12
    workup.ADDITIONDichloromethane (300 mL) and water (200 mL) were added
13. 13
    기타the layers were separated
14. 14
    건조The organic layer was dried (MgSO4)
15. 15
    기타the solvent was evaporated under reduced pressure

실험 절차

Benzyl bromide (52.4 mL, 441 mmol) was added to a solution of 4-(4-fluorophenyl)pyridine (Description 9, 50.87 g, 294 mmol) in acetone (500 mL) and mixture was heated under reflux for 3 days. The mixture was cooled to room temperature and the solid was collected, washed with acetone and diethyl ether and dried in vacuo. The solid was dissolved in methanol (400 mL) and water (100 mL), cooled to 0° C. and sodium borohydride (20.6 g, 542 mmol) was added in portions. The mixture was stirred at room temperature for 1 hour, then heated under reflux for 18 hours. The mixture was cooled and the solvent was evaporated under reduced pressure. Dichloromethane (300 mL) and water (200 mL) were added and the layers were separated. The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a light brown oil (61.5 g, 78%). m/z (ES+) 268 (M+1).

출처