반응 #716555

반응 방정식

water

methyl 4-cyano-2-hydroxy-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

1-(4-(chloromethyl)phenyl)-1H-pyrazole

tripotassium phosphate trihydrate

→

title compound

수율 22.5%

methyl 4-cyano-2-hydroxy-3-methyl-5-[4-(1H-pyrazol-1-yl)benzyl]benzoate

수율 22.5%

용매

1,4-dioxane

반응 조건

후처리

1. 1
   추출the mixture was extracted with ethyl acetate
2. 2
   건조The organic layer was dried over anhydrous sodium sulfate
3. 3
   기타the solvent was evaporated under reduced pressure
4. 4
   기타The residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether)

실험 절차

To a solution of methyl 4-cyano-2-hydroxy-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (3.50 g) in 1,4-dioxane (30.0 mL) were added 1-(4-(chloromethyl)phenyl)-1H-pyrazole (2.12 g), tripotassium phosphate trihydrate (5.90 g) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.34 g), and the mixture was stirred at 90° C. for 16 hr under nitrogen atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (0.86 g).

출처