반응 #548899

반응 방정식

tetrahydrofuran

magnesium

2-(p-bromobenzyloxy)tetrahydropyran

2-thiophenecarbonitrile

tetrahydrofuran

ammonium chloride

→

α-hydroxy-p-tolyl 2-thienyl ketone

반응 조건

후처리

1. 1
   온도refluxing Grignard-complex
2. 2
   기타previously prepared
3. 3
   workup.STIRRINGUpon completion, stirring
4. 4
   온도at reflux
5. 5
   온도The reaction mixture is cooled
6. 6
   workup.ADDITIONThe whole is poured onto water
7. 7
   추출the product is extracted with ether
8. 8
   세척The organic layer is washed four times with water
9. 9
   기타dried
10. 10
    여과filtered
11. 11
    기타an oil is separated
12. 12
    기타The ether is decanted
13. 13
    workup.DISSOLUTIONthe oily product is dissolved in 300 parts of water and 150 parts of concentrated hydrochloric acid solution
14. 14
    workup.STIRRINGThe solution is stirred with activated charcoal
15. 15
    여과filtered
16. 16
    workup.STIRRINGthe filtrate is stirred
17. 17
    온도refluxed for 10 minutes
18. 18
    추출The product is extracted with chloroform
19. 19
    세척The latter is washed with water
20. 20
    기타dried
21. 21
    여과filtered
22. 22
    기타evaporated
23. 23
    workup.DISTILLATIONThe residue is distilled

실험 절차

To a stirred and refluxing Grignard-complex, previously prepared starting from 7.2 parts of magnesium and 81.4 parts of 2-(p-bromobenzyloxy)tetrahydropyran in 200 parts of dry tetrahydrofuran, is added dropwise a solution of 32.7 parts of 2-thiophenecarbonitrile in 70 parts of dry tetrahydrofuran (exothermic reaction: reflux temperature is maintained). Upon completion, stirring at reflux is continued for 4 hours. The reaction mixture is cooled and decomposed with 150 parts of a saturated ammonium chloride solution at about 15° C. The whole is poured onto water and the product is extracted with ether. The organic layer is washed four times with water, dried, filtered and acidified with gaseous hydrogen chloride: an oil is separated. The ether is decanted and the oily product is dissolved in 300 parts of water and 150 parts of concentrated hydrochloric acid solution. The solution is stirred with activated charcoal, filtered and the filtrate is stirred and refluxed for 10 minutes. The product is extracted with chloroform. The latter is washed with water, dried, filtered and evaporated. The residue is distilled, yielding α-hydroxy-p-tolyl 2-thienyl ketone; b.p. 180°-190° C at 0.2 mm. pressure.

출처