Reacción #8738

Ecuación de reacción

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

KOH

2-ethoxyethanol

→

title compound

Rendimiento 68.0%

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

Rendimiento 68.0%

Disolventes

hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaReflux
2. 2
   TemperaturaHeat the reacton for an additional four hours
3. 3
   ExtracciónAdd water and extract the organics into ether
4. 4
   LavadoWash the ether phase with water
5. 5
   Secadodry (MgSO4)
6. 6
   Filtraciónfilter
7. 7
   Concentraciónconcentrate
8. 8
   Otroto yield an oil
9. 9
   OtroPurify the oil by column (alumina) chromatography
10. 10
    Lavadoelute with 15% ether in hexane
11. 11
    Otroto obtain white crystals
12. 12
    OtroRecrystallize the crystals from ether

Procedimiento

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.

Fuente