반응 #8738

반응 방정식

(3-bromothiophen-2-yl)-(3-methoxyphenyl)methanone oxime

KOH

2-ethoxyethanol

→

title compound

수율 68.0%

3-(3-methoxyphenyl)thieno[2,3-d]isoxazole

수율 68.0%

용매

hexane

반응 조건

후처리

1. 1
   온도Reflux
2. 2
   온도Heat the reacton for an additional four hours
3. 3
   추출Add water and extract the organics into ether
4. 4
   세척Wash the ether phase with water
5. 5
   건조dry (MgSO4)
6. 6
   여과filter
7. 7
   농축concentrate
8. 8
   기타to yield an oil
9. 9
   기타Purify the oil by column (alumina) chromatography
10. 10
    세척elute with 15% ether in hexane
11. 11
    기타to obtain white crystals
12. 12
    기타Recrystallize the crystals from ether

실험 절차

Reflux a mixture of (3-bromothiophen-2-yl)-(3-methoxyphenyl)methanone oxime (10 g, 0.032 mol), KOH (3.6 g, 0.064 mol dissolved in 10 mL water) and 2-ethoxyethanol (40 mL) under nitrogen for one hour at 105–110° C. Add copper chloride (0.16 g, 0.0016 mol) whereupon the reaction mixture becomes dark brown in color. Heat the reacton for an additional four hours. TLC shows that the reaction is complete. Add water and extract the organics into ether. Wash the ether phase with water, dry (MgSO4), filter and concentrate to yield an oil. Purify the oil by column (alumina) chromatography, and elute with 15% ether in hexane to obtain white crystals. Recrystallize the crystals from ether:hexane to yield the title compound (5 g, 68% Yield), m.p. 51–52° C.

출처