反应详情

A solution of 0.52 g (3.0 mmol) of 2,5-dimethylbenzoylacetonitrile, 0.45 g (3.0 mmol) of trimethylorthobutyrate and 0.632 g (0.58 mL, 6.2 mmol) of acetic anhydride in 5.0 mL of ethyl acetate was refluxed overnight and then cooled. The solvents were removed in vacuo and the residues were dissolved in 10 mL of ethanol. One-half of this solution, containing 1.5 mmol of 1-cyano-1-(2,5-dimethylbenzoyl)-3-methoxy-1-pentene was mixed with 0.7 mL (0.51 g, 5.0 mmol) of triethylamine and 0.37 g (1.50 mmol) of 2,6-dichloro-4-trifluoromethylphenylhydrazine and refluxed for 2.5 hours. The reaction mixture was cooled and partitioned between dilute hydrogen chloride and ethyl acetate. The organic phase was washed with water and then dried with brine and with magnesium sulfate. The solvent was evaporated to give an oil which was chromatographed on silica gel by the flash method eluting with 4:1 hexane/ethyl acetate to give the title compound as an amorphous foam. Anal. Calcd. for C22H20ON3CL2F3, 469.0935. Found: 469.0889.

1. temperaturecooled
2. customThe solvents were removed in vacuo
3. dissolutionthe residues were dissolved in 10 mL of ethanol
4. temperaturerefluxed for 2.5 hours
5. temperatureThe reaction mixture was cooled
6. custompartitioned between dilute hydrogen chloride and ethyl acetate
7. washThe organic phase was washed with water
8. dry with materialdried with brine and with magnesium sulfate
9. customThe solvent was evaporated
10. customto give an oil which
11. customwas chromatographed on silica gel by the flash method
12. washeluting with 4:1 hexane/ethyl acetate