반응 #1064459

반응 방정식

(E,E)-5-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]phenyl]-2,4-pentadien-1-al

2,4-oxazolidinedione

piperidine

→

5-[(E,E)-5-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]phenyl]-2,4pentadienylidene]-2,4-oxazolidinedione

용매

acetic acid

반응 조건

후처리

1. 1
   온도was refluxed under heating conditions for 15 hours
2. 2
   농축The reaction mixture was concentrated
3. 3
   workup.ADDITIONwater was added to the residue
4. 4
   추출followed by acidification with 2N HCl and subsequent extraction with ethyl acetate
5. 5
   세척The ethyl acetate layer was washed with water
6. 6
   건조dried (MgSO4)
7. 7
   농축concentrated

실험 절차

A mixture of (E,E)-5-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]phenyl]-2,4-pentadien-1-al (2.3 g), 2,4-oxazolidinedione (2.0 g), piperidine (0.596 g) and acetic acid (50 ml) was refluxed under heating conditions for 15 hours. The reaction mixture was concentrated; water was added to the residue, followed by acidification with 2N HCl and subsequent extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and then concentrated. The residue was subjected to silica gel chromatography to yield 5-[(E,E)-5-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]phenyl]-2,4pentadienylidene]-2,4-oxazolidinedione [mixture of the (E)- and (Z)-configurations](1.0 g, 33%) from the fraction eluted with chloroform-ethyl acetate (9:1, v/v), which was then recrystallized from chloroform-methanol to yield light yellow prisms having a melting point of 208°-210° C.

출처