反応 #966018

反応方程式

5-(3,5-dichlorophenyl)-3-(3-difluoromethoxy-4-iodophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

1,1,1,3,3,3-hexamethyldisilazane

diisopropylethylamine

N,N-dimethylformamide

hydrochloric acid

→

aimed product

4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-difluoromethoxy benzoic acid amide

反応条件

後処理

1. 1
   workup.WAITat room temperature for 3 days
2. 2
   workup.ADDITIONwas added
3. 3
   workup.STIRRINGstirred for 10 minutes
4. 4
   抽出extracted with ethyl acetate (10 mL×2)
5. 5
   洗浄The combined organic phases were washed with water
6. 6
   乾燥dried over saturated sodium chloride aqueous solution
7. 7
   workup.DISTILLATIONanhydrous sodium sulfate, and the solvent was distilled off under reduced pressure
8. 8
   その他The residue was purified with silica gel column chromatography that

実験手順

In a solution of 0.30 g of 5-(3,5-dichlorophenyl)-3-(3-difluoromethoxy-4-iodophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole, 0.80 mL of 1,1,1,3,3,3-hexamethyldisilazane and 0.20 mL of diisopropylethylamine in 10 ml of N,N-dimethylformamide, 0.062 g of 1,1′-bis(diphenylphosphino) ferrocene and 0.013 g of palladium (II) acetate were added, and stirred under carbon monoxide atmosphere at 90° C. for 12 hours and then at room temperature for 3 days. After the completion of the reaction, 10 mL of 1N hydrochloric acid was added, and stirred for 10 minutes, extracted with ethyl acetate (10 mL×2). The combined organic phases were washed with water, and then dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that were eluated with ethyl acetate-hexane (2:3) to obtain 0.30 g of the aimed product as yellow resinous substance.

出典