Reaktion #1146

Reaktionsgleichung

6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofurancarbaldehyde

2,4-oxazolidinedione

pyrrolidine

ethanol

→

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

Ausbeute 6.6%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated under refluxing conditions for 3 hours
2. 2
   Filtrationthe resulting crystals were collected by filtration
3. 3
   workup.DISSOLUTIONThe crystals were dissolved in tetrahydrofuran (100 ml)
4. 4
   workup.ADDITIONafter palladium-carbon (0.40 g) was added
5. 5
   Sonstigewas subjected to catalytic reduction at room temperature under an atmospheric pressure of 1 atm
6. 6
   FiltrationAfter the catalyst was filtered off
7. 7
   Einengenthe filtrate was concentrated under reduced pressure
8. 8
   WaschenFrom the fraction eluted with methanolchloroform (2:98

Vorschrift

A mixture of 6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofurancarbaldehyde (1.70 g), 2,4-oxazolidinedione (1.55 g), pyrrolidine (0.365 g) and ethanol (40 ml) was heated under refluxing conditions for 3 hours. The reaction mixture was poured over water; the resulting crystals were collected by filtration. The crystals were dissolved in tetrahydrofuran (100 ml); after palladium-carbon (0.40 g) was added, the mixture was subjected to catalytic reduction at room temperature under an atmospheric pressure of 1 atm. 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 methanolchloroform (2:98, v/v), crystals of 5-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranylmethyl]-2,4-oxazolidinedione (0.14 g, 6.6%) were obtained, which was then recrystallized from dichloromethane-methanol to yield colorless prisms having a melting point of 172° to 173° C.

Quelle