Реакция #8738

Уравнение реакции

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

KOH

2-ethoxyethanol

→

title compound

Выход 68.0%

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

Выход 68.0%

Растворители

hexane

Условия реакции

Обработка

1. 1
   ТемператураReflux
2. 2
   ТемператураHeat the reacton for an additional four hours
3. 3
   ЭкстракцияAdd water and extract the organics into ether
4. 4
   ПромывкаWash the ether phase with water
5. 5
   Сушкаdry (MgSO4)
6. 6
   Фильтрацияfilter
7. 7
   Концентрированиеconcentrate
8. 8
   Другоеto yield an oil
9. 9
   ДругоеPurify the oil by column (alumina) chromatography
10. 10
    Промывкаelute with 15% ether in hexane
11. 11
    Другоеto obtain white crystals
12. 12
    ДругоеRecrystallize the crystals from ether

Методика

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.

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