反応 #1064422

反応方程式

(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

収率 12.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   温度was refluxed under heating conditions for 8 hours
2. 2
   濃縮After the reaction mixture was concentrated
3. 3
   workup.ADDITIONchloroform was added to the residue
4. 4
   洗浄the mixture was then washed with 2N HCl and water
5. 5
   洗浄The organic layer was washed with water
6. 6
   乾燥dried (MgSO4)
7. 7
   濃縮concentrated
8. 8
   その他The crystal obtained from the fraction
9. 9
   洗浄eluted with ethyl acetate-chloroform (1:9, v/v)
10. 10
    workup.DISSOLUTIONwas dissolved in tetrahydrofuran (100 ml)
11. 11
    その他subjected to catalytic hydrogenation at 1 atm and room temperature in the presence of palladium-carbon (5%, 0.5 g)
12. 12
    ろ過After the catalyst was filtered off
13. 13
    濃縮the filtrate was concentrated under reduced pressure

実験手順

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.

出典