反应详情

To an ice-cooling solution of 2-butyl-4-chloroimidazole-5-carbaldehyde (0.19 g) in N,N-dimethylformamide (1 ml) was added sodium hydride (60% in oil; 44 mg), and the mixture was stirred for 10 minutes. To the mixture was then added 5-(4'-bromomethylbipenyl-2-yl-)-2,3-dihydro-3-triphenylmethyl-1,3,4-oxadiazol-2-one (0.57 g). The reaction mixture was stirred for 1.5 hour at room temperatures, which was diluted with water and extracted with ethyl acetate. The extract was washed with water and dried. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel. The crude product thus obtained was dissolved in trifluoroacetic acid (4 ml), and the solution was stirred for 30 minutes at 60° C. Trifluoroacetic acid was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with an aqueous solution of sodium hydrogencarbonate and dried. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel. Crude crystals thus obtained was recrystallized from ethylacetate-hexane to afford the title compound as colorless prisms (0.12 g, 27%), m.p.178°-179° C.

1. stirringThe reaction mixture was stirred for 1.5 hour at room temperatures, which
2. extractionextracted with ethyl acetate
3. washThe extract was washed with water
4. customdried
5. customThe solvent was evaporated under reduced pressure
6. customthe residue was purified by column chromatography on silica gel
7. customThe crude product thus obtained
8. stirringthe solution was stirred for 30 minutes at 60° C
9. customTrifluoroacetic acid was evaporated under reduced pressure
10. dissolutionThe residue was dissolved in ethyl acetate
11. washthe solution was washed with an aqueous solution of sodium hydrogencarbonate
12. customdried
13. customThe solvent was evaporated under reduced pressure
14. customthe residue was purified by column chromatography on silica gel
15. customCrude crystals thus obtained
16. customwas recrystallized from ethylacetate-hexane