反应详情

The crude of 4-(2-Pyridinyl)benzylalcohol was dissolved in 20 ml DCM, cooled using ice/methanol, triethylamine (1.25 ml, 8.9 mmole) was added followed by methanesulfonylchloride (0.7 ml, 8.9 mmole) added drop wise over 5 minutes. The reaction was allowed to stir at room temperature till the TLC indicated consumption of the starting material (3 hrs), after completion of the reaction, the reaction mixture was washed with water, saturated NaHCO3 solution, and saturated NaCl solution, dried using Na2SO4 and evaporated to produce yellow oil, the oil produced was dissolved in 25 ml of 90% ethanol, KCN (1.05 gm, 16.2 mmole) was then added and it was heated under reflux overnight. Ethanol was evaporated; solid was washed with 50 ml water and filtered. The solid was dissolved in 30 ml of conc. HCl, refluxed for 48 hr; charcoal was added refluxed for 1 hr, filtered. The HCl was evaporated, the solid formed was dissolved in 5 ml of water, NaOH 1 N was added drop wise while extracting with ethyl acetate, the ethyl acetate extract was dried with Na2SO4 and evaporated to produce white solid (0.6 gm, 35% in 3 steps) H1-NMR INOVA-500 (DMSO d6) δ 3.641 (s, 2H), 7.345 (t, J=6.0 Hz, 1H), 7.381 (d, J=8.5 Hz, 2H), 7.879 (t, J=8.0 Hz, 1H), 7.951 (d, J=8.0 Hz, 1H), 8.034 (d, J=8.0 Hz, 2H), 8.662 (d, J=4.0 Hz, 1H), 12.390 (s, 1H).

1. temperaturecooled
2. additionwas added
3. additionadded drop wise over 5 minutes
4. customconsumption of the starting material (3 hrs)
5. customafter completion of the reaction
6. washthe reaction mixture was washed with water, saturated NaHCO3 solution, and saturated NaCl solution
7. customdried
8. customevaporated
9. customto produce yellow oil
10. customthe oil produced
11. temperatureit was heated
12. temperatureunder reflux overnight
13. customEthanol was evaporated
14. washsolid was washed with 50 ml water
15. filtrationfiltered
16. dissolutionThe solid was dissolved in 30 ml of conc. HCl
17. temperaturerefluxed for 48 hr
18. additioncharcoal was added
19. temperaturerefluxed for 1 hr
20. filtrationfiltered
21. customThe HCl was evaporated
22. customthe solid formed
23. extractionwhile extracting with ethyl acetate
24. extractionthe ethyl acetate extract
25. dry with materialwas dried with Na2SO4
26. customevaporated
27. customto produce white solid (0.6 gm, 35% in 3 steps) H1-NMR