3-(4-氟-2-甲基苯基)-3-氧代丙腈

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 3-(4-fluoro-2-methylphenyl)-3-oxopropanenitrile (2.0 g, 11.3 mmol) in toluene (10 mL) was added (2-methylphenyl)hydrazine hydrochloride (2.15 g, 13.5 mmol). The reaction was stirred at 110° C. for 16 h, and then cooled to rt. It was concentrated under reduced pressure, and the residue was purified by silica gel flash chromatography (2:1-1:1=hexanes:ethyl acetate) to afford the product as a yellow oil (500 mg, 16%). 1H NMR (400 MHz, DMSO-d6) δ 2.12 (s, 3H), 2.44 (s, 3H), 5.74 (s, 1H), 7.02-7.14 (m, 2H), 7.34-7.43 (m, 4H), 7.52 (dd, 1H); ES-MS m/z 282.4 (MH+); HPLC RT (min) 3.36 cooled to rt It was concentrated under reduced pressure the residue was purified by silica gel flash chromatography (2:1-1:1=hexanes:ethyl acetate)

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 3-(4-fluoro-2-methylphenyl)-3-oxopropanenitrile (2.0 g, 11.3 mmol) in toluene (10 mL) was added (2-methylphenyl)hydrazine hydrochloride (2.15 g, 13.5 mmol). The reaction was stirred at 110° C. for 16 h, and then cooled to rt. It was concentrated under reduced pressure, and the residue was purified by silica gel flash chromatography (2:1-1:1=hexanes:ethyl acetate) to afford the product as a yellow oil (500 mg, 16%). 1H NMR (400 MHz, DMSO-d6) δ 2.12 (s, 3H), 2.44 (s, 3H), 5.74 (s, 1H), 7.02-7.14 (m, 2H), 7.34-7.43 (m, 4H), 7.52 (dd, 1H); ES-MS m/z 282.4 (MH+); HPLC RT (min) 3.36 cooled to rt It was concentrated under reduced pressure the residue was purified by silica gel flash chromatography (2:1-1:1=hexanes:ethyl acetate)

反应条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a suspension of hexane-washed sodium hydride (60% oil dispersion, 995 mg, 24.9 mmol) was added dropwise a THF solution (20 mL) of methyl 4-fluoro-2-methylbenzoate (3.8 g, 22.6 mmol) and anhydrous acetonitrile (2.4 mL, 45.2 mmol). The mixture was stirred at 70° C. for 16 h, and then cooled to rt. The resulting mixture was diluted with ethyl acetate (20 mL) and 1 N HCl (10 mL) and the layers were partitioned. The organic phase was washed with water (3×20 mL) and brine (20 mL), dried (Na2SO4), and concentrated under reduced pressure to afford 4.0 g of yellow oil, which was taken to the next step without further purification. ES-MS m/z 178.2 (MH+); HPLC RT (min) 2.22. cooled to rt the layers were partitioned The organic phase was washed with water (3×20 mL) and brine (20 mL) dried (Na2SO4) concentrated under reduced pressure

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 3-(4-fluoro-2-methylphenyl)-3-oxopropanenitrile (2.0 g, 11.3 mmol) in toluene (10 mL) was added (2-methylphenyl)hydrazine hydrochloride (2.15 g, 13.5 mmol). The reaction was stirred at 110° C. for 16 h, and then cooled to rt. It was concentrated under reduced pressure, and the residue was purified by silica gel flash chromatography (2:1-1:1=hexanes:ethyl acetate) to afford the product as a yellow oil (500 mg, 16%). 1H NMR (400 MHz, DMSO-d6) δ 2.12 (s, 3H), 2.44 (s, 3H), 5.74 (s, 1H), 7.02-7.14 (m, 2H), 7.34-7.43 (m, 4H), 7.52 (dd, 1H); ES-MS m/z 282.4 (MH+); HPLC RT (min) 3.36 cooled to rt It was concentrated under reduced pressure the residue was purified by silica gel flash chromatography (2:1-1:1=hexanes:ethyl acetate)

反应条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a suspension of hexane-washed sodium hydride (60% oil dispersion, 995 mg, 24.9 mmol) was added dropwise a THF solution (20 mL) of methyl 4-fluoro-2-methylbenzoate (3.8 g, 22.6 mmol) and anhydrous acetonitrile (2.4 mL, 45.2 mmol). The mixture was stirred at 70° C. for 16 h, and then cooled to rt. The resulting mixture was diluted with ethyl acetate (20 mL) and 1 N HCl (10 mL) and the layers were partitioned. The organic phase was washed with water (3×20 mL) and brine (20 mL), dried (Na2SO4), and concentrated under reduced pressure to afford 4.0 g of yellow oil, which was taken to the next step without further purification. ES-MS m/z 178.2 (MH+); HPLC RT (min) 2.22. cooled to rt the layers were partitioned The organic phase was washed with water (3×20 mL) and brine (20 mL) dried (Na2SO4) concentrated under reduced pressure