6-溴-2-乙基-2,3-二氢色烯-4-one

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The mixture of 1-(5-bromo-2-hydroxyphenyl)ethanone (10 g, 46.50 mmol), propionaldehyde (6.7 mL, 93 mmol), pyrrolidine (3.9 mL, 47 mmol), and acetic acid (3.2 mL, 56 mmol) in toluene (20 mL) was heated to 60° C. for 18 hours. After cooling to room temperature, the mixture was concentrated in vacuo. The mixture was diluted with diethyl ether and 1M aqueous HCl. The phases were separated. The organic phase was washed with 1M aqueous NaOH, then brine. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. Purification with silicagel column chromatography (EtOAc-hexane, a linear gradient of EtOAc from 1 to 10%) afforded 6-bromo-2-ethyl-2,3-dihydro-4H-chromen-4-one (3.92 g). After cooling to room temperature the mixture was concentrated in vacuo The mixture was diluted with diethyl ether and 1M aqueous HCl The phases were separated The organic phase was washed with 1M aqueous NaOH The organic phase was dried over Na2SO4 filtered concentrated in vacuo Purification with silicagel column chromatography (EtOAc-hexane

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The mixture of 1-(5-bromo-2-hydroxyphenyl)ethanone (10 g, 46.50 mmol), propionaldehyde (6.7 mL, 93 mmol), pyrrolidine (3.9 mL, 47 mmol), and acetic acid (3.2 mL, 56 mmol) in toluene (20 mL) was heated to 60° C. for 18 hours. After cooling to room temperature, the mixture was concentrated in vacuo. The mixture was diluted with diethyl ether and 1M aqueous HCl. The phases were separated. The organic phase was washed with 1M aqueous NaOH, then brine. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. Purification with silicagel column chromatography (EtOAc-hexane, a linear gradient of EtOAc from 1 to 10%) afforded 6-bromo-2-ethyl-2,3-dihydro-4H-chromen-4-one (3.92 g). After cooling to room temperature the mixture was concentrated in vacuo The mixture was diluted with diethyl ether and 1M aqueous HCl The phases were separated The organic phase was washed with 1M aqueous NaOH The organic phase was dried over Na2SO4 filtered concentrated in vacuo Purification with silicagel column chromatography (EtOAc-hexane

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The mixture of 1-(5-bromo-2-hydroxyphenyl)ethanone (10 g, 46.50 mmol), propionaldehyde (6.7 mL, 93 mmol), pyrrolidine (3.9 mL, 47 mmol), and acetic acid (3.2 mL, 56 mmol) in toluene (20 mL) was heated to 60° C. for 18 hours. After cooling to room temperature, the mixture was concentrated in vacuo. The mixture was diluted with diethyl ether and 1M aqueous HCl. The phases were separated. The organic phase was washed with 1M aqueous NaOH, then brine. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. Purification with silicagel column chromatography (EtOAc-hexane, a linear gradient of EtOAc from 1 to 10%) afforded 6-bromo-2-ethyl-2,3-dihydro-4H-chromen-4-one (3.92 g). After cooling to room temperature the mixture was concentrated in vacuo The mixture was diluted with diethyl ether and 1M aqueous HCl The phases were separated The organic phase was washed with 1M aqueous NaOH The organic phase was dried over Na2SO4 filtered concentrated in vacuo Purification with silicagel column chromatography (EtOAc-hexane

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The mixture of 1-(5-bromo-2-hydroxyphenyl)ethanone (10 g, 46.50 mmol), propionaldehyde (6.7 mL, 93 mmol), pyrrolidine (3.9 mL, 47 mmol), and acetic acid (3.2 mL, 56 mmol) in toluene (20 mL) was heated to 60° C. for 18 hours. After cooling to room temperature, the mixture was concentrated in vacuo. The mixture was diluted with diethyl ether and 1M aqueous HCl. The phases were separated. The organic phase was washed with 1M aqueous NaOH, then brine. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. Purification with silicagel column chromatography (EtOAc-hexane, a linear gradient of EtOAc from 1 to 10%) afforded 6-bromo-2-ethyl-2,3-dihydro-4H-chromen-4-one (3.92 g). After cooling to room temperature the mixture was concentrated in vacuo The mixture was diluted with diethyl ether and 1M aqueous HCl The phases were separated The organic phase was washed with 1M aqueous NaOH The organic phase was dried over Na2SO4 filtered concentrated in vacuo Purification with silicagel column chromatography (EtOAc-hexane

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The mixture of 1-(5-bromo-2-hydroxyphenyl)ethanone (10 g, 46.50 mmol), propionaldehyde (6.7 mL, 93 mmol), pyrrolidine (3.9 mL, 47 mmol), and acetic acid (3.2 mL, 56 mmol) in toluene (20 mL) was heated to 60° C. for 18 hours. After cooling to room temperature, the mixture was concentrated in vacuo. The mixture was diluted with diethyl ether and 1M aqueous HCl. The phases were separated. The organic phase was washed with 1M aqueous NaOH, then brine. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. Purification with silicagel column chromatography (EtOAc-hexane, a linear gradient of EtOAc from 1 to 10%) afforded 6-bromo-2-ethyl-2,3-dihydro-4H-chromen-4-one (3.92 g). After cooling to room temperature the mixture was concentrated in vacuo The mixture was diluted with diethyl ether and 1M aqueous HCl The phases were separated The organic phase was washed with 1M aqueous NaOH The organic phase was dried over Na2SO4 filtered concentrated in vacuo Purification with silicagel column chromatography (EtOAc-hexane