Реакция #1145

Уравнение реакции

5-[6-(5-methyl-2-phenyl-4-oxazolyl-methoxy)-2-benzofuranylmethylidene]-2,4-thiazolidinedione

→

5-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranylmethyl]-2,4-thiazolidinedione

Выход 38.0%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеwas subjected to catalytic reduction at room temperature under a hydrogen
2. 2
   Другоеfor 8 hours
3. 3
   ФильтрацияAfter the catalyst was filtered off
4. 4
   ФильтрацияAfter the catalyst was filtered off
5. 5
   Концентрированиеthe filtrate was concentrated under reduced pressure
6. 6
   ПромывкаFrom the fraction eluted with ethyl acetate-chloroform (1:5

Методика

A mixture of 5-[6-(5-methyl-2-phenyl-4-oxazolyl-methoxy)-2-benzofuranylmethylidene]-2,4-thiazolidinedione (0.80 g), palladium-carbon (5%, 1.60 g) and tetrahydrofuran (250 ml) was subjected to catalytic reduction at room temperature under a hydrogen pressure of 3.2 kgf/cm2 for 8 hours. After the catalyst was filtered off, the filtrate was subjected to catalytic reduction under constant conditions for additional 16 hours. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure; the residue was subjected to silica gel column chromatography. From the fraction eluted with ethyl acetate-chloroform (1:5, v/v), crystals of 5-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranylmethyl]-2,4-thiazolidinedione (0.305 g, 38%) were obtained, which was then recrystallized from dichloromethane-methanol to yield yellow needles having a melting point of 179° to 180° C.

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