반응 #1064422

반응 방정식

(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

수율 12.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도was refluxed under heating conditions for 8 hours
2. 2
   농축After the reaction mixture was concentrated
3. 3
   workup.ADDITIONchloroform was added to the residue
4. 4
   세척the mixture was then washed with 2N HCl and water
5. 5
   세척The organic layer was washed with water
6. 6
   건조dried (MgSO4)
7. 7
   농축concentrated
8. 8
   기타The crystal obtained from the fraction
9. 9
   세척eluted with ethyl acetate-chloroform (1:9, v/v)
10. 10
    workup.DISSOLUTIONwas dissolved in tetrahydrofuran (100 ml)
11. 11
    기타subjected to catalytic hydrogenation at 1 atm and room temperature in the presence of palladium-carbon (5%, 0.5 g)
12. 12
    여과After the catalyst was filtered off
13. 13
    농축the filtrate was concentrated under reduced pressure

실험 절차

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.

출처