反应详情

温度

80 °C

A mixture of 3-(1-chloro-3-methylbutyl)-2-methyl-5-phenylfuran (1.1 g), methyl 4-amino-2-methylbenzoate (1.1 g), sodium carbonate (0.6 g) and sodium iodide (2.4 g) in N,N-dimethylacetamide (20 mL) was stirred overnight at 80° C. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was dissolved in methanol (5 mL) and tetrahydrofuran (5 mL), 2N lithium hydroxide (4 mL) was added, and the mixture was stirred at 70° C. for 6 hr. The reaction mixture was poured into water, and the mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (10% ethyl acetate/hexane to 50% ethyl acetate/hexane) to give the title compound (0.5 g, 33%) as an oil.

1. extractionthe mixture was extracted with ethyl acetate
2. washThe organic layer was washed with saturated brine
3. dry with materialdried over magnesium sulfate
4. customThe solvent was evaporated under reduced pressure
5. dissolutionthe residue was dissolved in methanol (5 mL)
6. additiontetrahydrofuran (5 mL), 2N lithium hydroxide (4 mL) was added
7. stirringthe mixture was stirred at 70° C. for 6 hr
8. additionThe reaction mixture was poured into water
9. extractionextracted with ethyl acetate
10. washThe organic layer was washed with saturated brine
11. dry with materialdried over magnesium sulfate
12. customThe solvent was evaporated under reduced pressure
13. customthe residue was purified by silica gel chromatography (10% ethyl acetate/hexane to 50% ethyl acetate/hexane)