반응 #346106

반응 방정식

tetrahydrofuran

magnesium

2-(p-bromo-α-methylbenzyloxy)tetrahydropyran

2-thiophenecarbonitrile

tetrahydrofuran

ammonium chloride

→

p-(1-hydroxyethyl)phenyl 2-thienyl ketone

반응 조건

후처리

1. 1
   기타A Grignard-complex is formed
2. 2
   온도To this stirring and refluxing complex
3. 3
   온도at reflux
4. 4
   workup.STIRRINGThe reaction mixture is stirred overnight at room temperature
5. 5
   온도After cooling
6. 6
   workup.ADDITIONThe whole is poured onto water
7. 7
   추출extracted with ether
8. 8
   세척The organic phase is washed four times with water
9. 9
   기타dried
10. 10
    여과filtered and upon acidification of the filtrate with 2-propanol, previously saturated with gaseous hydrogen chloride
11. 11
    기타an oil is separated
12. 12
    기타The ether is decanted
13. 13
    기타the oil is triturated twice in ether
14. 14
    기타The latter is decanted each time
15. 15
    workup.DISSOLUTIONthe oily product is dissolved in water
16. 16
    workup.ADDITIONConcentrated hydrochloric acid solution is added (150 parts)
17. 17
    workup.STIRRINGthe whole is stirred with activated charcoal
18. 18
    여과The latter is filtered off
19. 19
    workup.WAITthe filtrate is boiled for 10 minutes
20. 20
    추출extracted with ether
21. 21
    세척The combined extracts are washed with water
22. 22
    기타dried
23. 23
    여과filtered
24. 24
    기타evaporated

실험 절차

A Grignard-complex is formed starting from 7.2 parts of magnesium and 93.9 parts of 2-(p-bromo-α-methylbenzyloxy)tetrahydropyran in 200 parts of dry tetrahydrofuran. To this stirring and refluxing complex is added dropwise a solution of 32.7 parts of 2-thiophenecarbonitrile in 70 parts of dry tetrahydrofuran and stirring at reflux is continued for 4 hours. The reaction mixture is stirred overnight at room temperature. After cooling, it is decomposed with 150 parts of a saturated ammonium chloride solution at a temperature of about 15° C. The whole is poured onto water and extracted with ether. The organic phase is washed four times with water, dried, filtered and upon acidification of the filtrate with 2-propanol, previously saturated with gaseous hydrogen chloride, an oil is separated. The ether is decanted and the oil is triturated twice in ether. The latter is decanted each time and the oily product is dissolved in water. Concentrated hydrochloric acid solution is added (150 parts) and the whole is stirred with activated charcoal. The latter is filtered off and the filtrate is boiled for 10 minutes and extracted with ether. The combined extracts are washed with water, dried, filtered and evaporated, yielding p-(1-hydroxyethyl)phenyl 2-thienyl ketone, as an oily residue.

출처