反应详情

A mixture of 4-tert-butyl-2-(5-formylbenzofuran-2-yl)thiazole (1.83 g) and triethyl phosphonoacetate (1.53 ml) in the mixed solvent of tetrahydrofuran (10 ml) and N,N-dimethylformamide (10 ml) was stirred under ice-cooling. After several minutes, potassium tert-butoxide was added to the mixture, which was stirred for 1 hour at same temperature. The resulting mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with a mixture of n-hexane and ethyl acetate. The fractions containing the objective compound were combined and concentrated under reduced pressure to give ethyl (E)-3-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]propenoate (0.68 g).

1. temperaturecooling
2. waitAfter several minutes
3. stirringwas stirred for 1 hour at same temperature
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customto give a syrup
9. washeluted with a mixture of n-hexane and ethyl acetate
10. additionThe fractions containing the objective compound
11. concentrationconcentrated under reduced pressure