2-(4-chlorophenyl)-3-cyclopropyl-3-oxopropanenitrile

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(4-Chlorophenyl)-3-cyclopropyl-3-oxopropanenitrile(7.74 g), hydrazine hydrate (3.5 mL) and acetic acid (7.5 mL) are dissolved in a toluene solvent and stirred for 16 hours while heating. Upon completion of reaction, after cooling to room temperature, the solvent is removed by distillation under reduced pressure. The remainder is extracted with water and ethyl acetate. The extracted organic layer is dehydrated and distilled under reduced pressure. The remainder is purified by column chromatography to yield 5.2 g of the target compound. 1H NMR (CDCl3, 300 MHz): δ 7.40 (m, 4H), 3.75 (br, 2H), 1.86 (m, 1H) 0.93 (m, 2H), 0.65 (m, 2H). while heating Upon completion of reaction the solvent is removed by distillation under reduced pressure The remainder is extracted with water and ethyl acetate distilled under reduced pressure The remainder is purified by column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(4-Chlorophenyl)-3-cyclopropyl-3-oxopropanenitrile(7.74 g), hydrazine hydrate (3.5 mL) and acetic acid (7.5 mL) are dissolved in a toluene solvent and stirred for 16 hours while heating. Upon completion of reaction, after cooling to room temperature, the solvent is removed by distillation under reduced pressure. The remainder is extracted with water and ethyl acetate. The extracted organic layer is dehydrated and distilled under reduced pressure. The remainder is purified by column chromatography to yield 5.2 g of the target compound. 1H NMR (CDCl3, 300 MHz): δ 7.40 (m, 4H), 3.75 (br, 2H), 1.86 (m, 1H) 0.93 (m, 2H), 0.65 (m, 2H). while heating Upon completion of reaction the solvent is removed by distillation under reduced pressure The remainder is extracted with water and ethyl acetate distilled under reduced pressure The remainder is purified by column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(4-Chlorophenyl)acetonitrile (5.74 g) is dissolved in 120 mL of THF at 0° C. After adding 60% NaH (4.2 g, 2.7 eq), the reaction mixture is stirred for 10 minutes. Ethylcyclopropane carboxylate is added and the mixture is stirred overnight. The reaction is stopped by adding acetic acid (5 mL) and water. The aqueous layer is extracted with ethyl acetate (50 mL×3). The collected organic layer is washed with brine and dehydrated with MgSO4. The dehydrated organic layer is concentrated by distillation under reduced pressure and purified by column chromatography to yield 7.74 g of the target compound. 1H NMR (CDCl3, 300 MHz): δ 7.42 (d, J=8.7 Hz, 2H), 7.34 (d, J=8.7 Hz, 2H), 4.79 (s, 1H), 2.10 (m, 1H) 1.16 (m, 2H), 1.03 (m, 2H). the mixture is stirred overnight The aqueous layer is extracted with ethyl acetate (50 mL×3) The collected organic layer is washed with brine The dehydrated organic layer is concentrated by distillation under reduced pressure purified by column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(4-Chlorophenyl)-3-cyclopropyl-3-oxopropanenitrile(7.74 g), hydrazine hydrate (3.5 mL) and acetic acid (7.5 mL) are dissolved in a toluene solvent and stirred for 16 hours while heating. Upon completion of reaction, after cooling to room temperature, the solvent is removed by distillation under reduced pressure. The remainder is extracted with water and ethyl acetate. The extracted organic layer is dehydrated and distilled under reduced pressure. The remainder is purified by column chromatography to yield 5.2 g of the target compound. 1H NMR (CDCl3, 300 MHz): δ 7.40 (m, 4H), 3.75 (br, 2H), 1.86 (m, 1H) 0.93 (m, 2H), 0.65 (m, 2H). while heating Upon completion of reaction the solvent is removed by distillation under reduced pressure The remainder is extracted with water and ethyl acetate distilled under reduced pressure The remainder is purified by column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(4-Chlorophenyl)acetonitrile (5.74 g) is dissolved in 120 mL of THF at 0° C. After adding 60% NaH (4.2 g, 2.7 eq), the reaction mixture is stirred for 10 minutes. Ethylcyclopropane carboxylate is added and the mixture is stirred overnight. The reaction is stopped by adding acetic acid (5 mL) and water. The aqueous layer is extracted with ethyl acetate (50 mL×3). The collected organic layer is washed with brine and dehydrated with MgSO4. The dehydrated organic layer is concentrated by distillation under reduced pressure and purified by column chromatography to yield 7.74 g of the target compound. 1H NMR (CDCl3, 300 MHz): δ 7.42 (d, J=8.7 Hz, 2H), 7.34 (d, J=8.7 Hz, 2H), 4.79 (s, 1H), 2.10 (m, 1H) 1.16 (m, 2H), 1.03 (m, 2H). the mixture is stirred overnight The aqueous layer is extracted with ethyl acetate (50 mL×3) The collected organic layer is washed with brine The dehydrated organic layer is concentrated by distillation under reduced pressure purified by column chromatography