反应详情

Into a 25 ml round bottom flask equpped with magnetic stirrer, thermometer, reflux condenser and heating mantle is placed a solution containing 0.27 g (0.005 moles) of sodium methoxide in 3 ml of absolute methanol. With stirring and while maintaining the temperature at 25° C-30° C, 0.57 g (0.005 moles) of 2-methyl-3-furan thiol in 3 ml absolute methanol is added. The reaction mass is stirred for a period of 10 minutes. 0.86 g of benzyl bromide dissolved in 2 ml absolute methanol is then added to the reaction mass with stirring at 25° C. The reaction mass is heated to reflux (50° C-60° C) and maintained at this temperature with stirring for a period of 4 hours. The reaction mass is then allowed to cool down to room temperature and is admixed with 10 ml of water with stirring. The reaction mass is neutralized to a pH of 5-6 with one drop of 10% hydrochloric acid and 5 ml hexane is added with stirring. The mass is then transferred to a separatory funnel and the organic and aqueous phases are separated. The aqueous phase is diluted with 5 ml water and extracted with 7 ml of n-hexne. The hexane extracts are combined, washed with 5 ml saturated sodium chloride, dried over anhydrous sodium sulfate, and gravity filtered. The resulting solution is then concentrated to an amber oil using rotary evaporation under a water aspirator vacuum. NMR, IR and Mass Spectral analyses confirm that the major product isolated by GLC trapping has the structure: ##STR32##

1. customInto a 25 ml round bottom flask equpped with magnetic stirrer
2. temperaturethermometer, reflux condenser
3. temperatureheating mantle
4. temperaturewhile maintaining the temperature at 25° C-30° C
5. stirringThe reaction mass is stirred for a period of 10 minutes
6. additionis then added to the reaction mass
7. stirringwith stirring at 25° C
8. temperatureThe reaction mass is heated
9. temperatureto reflux (50° C-60° C)
10. temperaturemaintained at this temperature
11. stirringwith stirring for a period of 4 hours
12. stirringwith stirring
13. additionis added
14. stirringwith stirring
15. customThe mass is then transferred to a separatory funnel
16. customthe organic and aqueous phases are separated
17. additionThe aqueous phase is diluted with 5 ml water
18. extractionextracted with 7 ml of n-hexne
19. washwashed with 5 ml saturated sodium chloride
20. dry with materialdried over anhydrous sodium sulfate, and gravity
21. filtrationfiltered
22. concentrationThe resulting solution is then concentrated to an amber oil
23. customevaporation under a water
24. customisolated by GLC trapping