反応 #156282

反応方程式

sodium hydroxide

water ethyl acetate

(2E)-1-(4-bromo-2-nitrophenyl)-3-(dimethylamino)prop-2-en-1-one

cyclopentylhydrazine hydrochloride

→

5-(4-bromo-2-nitrophenyl)-1-cyclopentyl-1H-pyrazole

収率 72.7%

溶媒

acetic acid

反応条件

後処理

1. 1
   その他The aqueous layer was separated
2. 2
   洗浄the organic layer was washed with water and saturated brine
3. 3
   乾燥dried over anhydrous magnesium sulfate
4. 4
   その他The solvent was evaporated under reduced pressure
5. 5
   その他the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

実験手順

Under a nitrogen atmosphere, to a solution of 1.15 g of (2E)-1-(4-bromo-2-nitrophenyl)-3-(dimethylamino)prop-2-en-1-one in 9.2 mL of acetic acid was added 1.05 g of cyclopentylhydrazine hydrochloride, followed by stirring at room temperature for 60 hours. The reaction mixture was poured into a mixture of water/ethyl acetate, followed by adjusting to pH 10 with a 6 M aqueous sodium hydroxide solution. The aqueous layer was separated, and then the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 940 mg of 5-(4-bromo-2-nitrophenyl)-1-cyclopentyl-1H-pyrazole.

出典