Reaktion #1064422

Reaktionsgleichung

(E)-4-[2-[5-methyl-2-(2-naphthyl)-4-oxazolyl]vinyl]cinnamaldehyde

2,4-oxazolidinedione

piperidine

ethanol

→

5-[3-[4-[2-[5-methyl-2-(2-naphthyl)-4-oxazolyl]ethyl]phenyl]propyl]-2,4-oxazolidinedione

Ausbeute 12.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed under heating conditions for 8 hours
2. 2
   EinengenAfter the reaction mixture was concentrated
3. 3
   workup.ADDITIONchloroform was added to the residue
4. 4
   Waschenthe mixture was then washed with 2N HCl and water
5. 5
   WaschenThe organic layer was washed with water
6. 6
   Trocknendried (MgSO4)
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe crystal obtained from the fraction
9. 9
   Wascheneluted with ethyl acetate-chloroform (1:9, v/v)
10. 10
    workup.DISSOLUTIONwas dissolved in tetrahydrofuran (100 ml)
11. 11
    Sonstigesubjected to catalytic hydrogenation at 1 atm and room temperature in the presence of palladium-carbon (5%, 0.5 g)
12. 12
    FiltrationAfter the catalyst was filtered off
13. 13
    Einengenthe filtrate was concentrated under reduced pressure

Vorschrift

A mixture of (E)-4-[2-[5-methyl-2-(2-naphthyl)-4-oxazolyl]vinyl]cinnamaldehyde (2.00 g), 2,4-oxazolidinedione (1.11 g), piperidine (0.23 g), ethanol (100 ml) and tetrahydrofuran (50 ml) was refluxed under heating conditions for 8 hours. After the reaction mixture was concentrated, chloroform was added to the residue; the mixture was then washed with 2N HCl and water. The organic layer was washed with water, dried (MgSO4) and then concentrated. The residue was subjected to silica gel column chromatography. The crystal obtained from the fraction eluted with ethyl acetate-chloroform (1:9, v/v) was dissolved in tetrahydrofuran (100 ml), and subjected to catalytic hydrogenation at 1 atm and room temperature in the presence of palladium-carbon (5%, 0.5 g). After the catalyst was filtered off, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to yield 5-[3-[4-[2-[5-methyl-2-(2-naphthyl)-4-oxazolyl]ethyl]phenyl]propyl]-2,4-oxazolidinedione (0.29 g, 12%) from the fraction eluted with methanol-chloroform (2:98, v/v), which was then recrystallized from dichloromethane-isopropyl ether to yield a colorless prisms having a melting point of 168°-169° C.

Quelle