反应详情

In a solution of 1.70 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(hydroxymethyl)benzoic acid amide in 20 ml of dichloromethane, 0.68 g of thionyl chloride was added with stirring at room temperature, stirred at the same temperature for 2 hours, then the solvent was distilled off under reduced pressure, and the residue was dissolved in 10 ml of tetrahydrofuran. In 0.33 g of 60% oily sodium hydride suspended in 30 ml of tetrahydrofuran, 1.50 g of 2,2,2-trifluoroethanol was added dropwise with stirring under ice cooling, and stirred at the same temperature for 10 minutes. Then, the solution of benzoic acid chloride in tetrahydrofuran prepared above was added dropwise in the reaction mixture with stirring under ice cooling, after the completion of the addition, continued to stir at room temperature for 1 hour. After the completion of the reaction, 50 ml of water was added in the reaction mixture, extracted with ethyl acetate (70 ml×1), and the organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (2:3) to obtain 1.20 g of the aimed product as colorless resinous substance.

1. stirringstirred at the same temperature for 2 hours
2. distillationthe solvent was distilled off under reduced pressure
3. dissolutionthe residue was dissolved in 10 ml of tetrahydrofuran
4. addition1.50 g of 2,2,2-trifluoroethanol was added dropwise
5. stirringwith stirring under ice cooling
6. stirringstirred at the same temperature for 10 minutes
7. customThen, the solution of benzoic acid chloride in tetrahydrofuran prepared
8. additionabove was added dropwise in the reaction mixture
9. stirringwith stirring under ice cooling
10. additionafter the completion of the addition
11. stirringto stir at room temperature for 1 hour
12. additionwas added in the reaction mixture
13. extractionextracted with ethyl acetate (70 ml×1)
14. dry with materialdried with saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order
15. distillationthe solvent was distilled off under reduced pressure
16. customThe residue was purified with silica gel column chromatography that