反应详情

温度

-78 °C

Under nitrogen atmosphere, to a solution of N-methyl-N-methoxy-5-(4-methylphenyl)furan-2-carboxamide (2.5 g) in tetrahydrofuran (20 ml) was added duisobutylaluminum hydride (1.01M toluene solution) (15 ml) at -78° C., and the mixture was stirred at -78° C. for 10 minutes and then at 0° C. for 15 minutes. To the reaction mixture was added 1N hydrochloric acid to stop the reaction, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:5→1:4) to give crude product (1.49 g). A solution of the crude aldehyde (1.49 g) and methyl (triphenylphosphoranilidene)acetate (2.67 g) in toluene (30 ml) was refluxed under nitrogen atmosphere for 1 hour and cooled. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:9→1:5) to give methyl (E)-3-[5-(4-methylphenyl)furan-2-yl]acrylate (1.63 g) as pale yellow crystals.

1. waitat 0° C. for 15 minutes
2. customthe reaction
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with saturated sodium chloride solution
5. dry with materialdried with magnesium sulfate
6. concentrationconcentrated
7. customThe residue was separated
8. custompurified with column chromatography (ethyl acetate/hexane=1:5→1:4)
9. customto give crude product (1.49 g)
10. temperaturecooled
11. extractionthe mixture was extracted with ethyl acetate
12. washThe organic layer was washed with saturated sodium chloride solution
13. dry with materialdried with magnesium sulfate
14. concentrationconcentrated under reduced pressure
15. customThe residue was separated
16. custompurified with column chromatography (ethyl acetate/hexane=1:9→1:5)