Réaction #8738

Équation de réaction

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

KOH

2-ethoxyethanol

→

title compound

Rendement 68.0%

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

Rendement 68.0%

Solvants

hexane

Conditions de réaction

Traitement

1. 1
   TempératureReflux
2. 2
   TempératureHeat the reacton for an additional four hours
3. 3
   ExtractionAdd water and extract the organics into ether
4. 4
   LavageWash the ether phase with water
5. 5
   Séchagedry (MgSO4)
6. 6
   Filtrationfilter
7. 7
   Concentrationconcentrate
8. 8
   Autreto yield an oil
9. 9
   AutrePurify the oil by column (alumina) chromatography
10. 10
    Lavageelute with 15% ether in hexane
11. 11
    Autreto obtain white crystals
12. 12
    AutreRecrystallize the crystals from ether

Mode opératoire

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.

Source