methyl (E)-4-(dimethylamino)but-2-enoate

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl (2E)-4-(dimethylamino)but-2-enoate (3.4 g, 23.7 mmol) was dissolved in methanol (25 mL). A solution of sodium hydroxide (0.95 g, 23.7 mmol) in water (7 mL) was added, and the mixture was heated to 50° C. for 1 h. The pH was then adjusted to 2 with conc. hydrochloric acid. The solution was concentrated to dryness, and the residue was triturated with ethanol (30 mL). It was filtered, and the solution was concentrated in vacuo. The residue was triturated with 2-propanol, and the precipitate was collected by suction filtration and dried to yield 2.00 g (51%) of the title compound. The solution was concentrated to dryness the residue was triturated with ethanol (30 mL) It was filtered the solution was concentrated in vacuo The residue was triturated with 2-propanol the precipitate was collected by suction filtration dried

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

実験手順: Trithylamine (37.5 ml, 0.27 mol, 2.8 equiv) was dissolved in THF (100 ml), and dimethylamine hydrochloride (9.3 g, 0.114 mol, 1.2 equiv) was added. Methyl 4-bromocrotonate (20 g, 85% purity, 0.095 mol, 1.00 equiv) in 100 ml of THF was added drop-wise to the resulting solution at room temperature while stirring. The reaction mixture was allowed to react overnight at room temperature. The reaction mixture was filtered, and the filtrate was evaporated under reduced pressure to give yellow oil. The oil was dissolved in 50 ml of isopropanol, and hydrogen chloride was added until pH 2.0 was reached. The white solid was formed and filtered and dried to give 7.1 g product. MS (ESI) m/z: 563 (M+1). to react overnight at room temperature The reaction mixture was filtered the filtrate was evaporated under reduced pressure to give yellow oil The white solid was formed filtered dried

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

実験手順: Trithylamine (37.5 ml, 0.27 mol, 2.8 equiv) was dissolved in THF (100 ml), and dimethylamine hydrochloride (9.3 g, 0.114 mol, 1.2 equiv) was added. Methyl 4-bromocrotonate (20 g, 85% purity, 0.095 mol, 1.00 equiv) in 100 ml of THF was added drop-wise to the resulting solution at room temperature while stirring. The reaction mixture was allowed to react overnight at room temperature. The reaction mixture was filtered, and the filtrate was evaporated under reduced pressure to give yellow oil. The oil was dissolved in 50 ml of isopropanol, and hydrogen chloride was added until pH 2.0 was reached. The white solid was formed and filtered and dried to give 7.1 g product. MS (ESI) m/z: 563 (M+1). to react overnight at room temperature The reaction mixture was filtered the filtrate was evaporated under reduced pressure to give yellow oil The white solid was formed filtered dried

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

実験手順: Trithylamine (37.5 ml, 0.27 mol, 2.8 equiv) was dissolved in THF (100 ml), and dimethylamine hydrochloride (9.3 g, 0.114 mol, 1.2 equiv) was added. Methyl 4-bromocrotonate (20 g, 85% purity, 0.095 mol, 1.00 equiv) in 100 ml of THF was added drop-wise to the resulting solution at room temperature while stirring. The reaction mixture was allowed to react overnight at room temperature. The reaction mixture was filtered, and the filtrate was evaporated under reduced pressure to give yellow oil. The oil was dissolved in 50 ml of isopropanol, and hydrogen chloride was added until pH 2.0 was reached. The white solid was formed and filtered and dried to give 7.1 g product. MS (ESI) m/z: 563 (M+1). to react overnight at room temperature The reaction mixture was filtered the filtrate was evaporated under reduced pressure to give yellow oil The white solid was formed filtered dried

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl (2E)-4-(dimethylamino)but-2-enoate (3.4 g, 23.7 mmol) was dissolved in methanol (25 mL). A solution of sodium hydroxide (0.95 g, 23.7 mmol) in water (7 mL) was added, and the mixture was heated to 50° C. for 1 h. The pH was then adjusted to 2 with conc. hydrochloric acid. The solution was concentrated to dryness, and the residue was triturated with ethanol (30 mL). It was filtered, and the solution was concentrated in vacuo. The residue was triturated with 2-propanol, and the precipitate was collected by suction filtration and dried to yield 2.00 g (51%) of the title compound. The solution was concentrated to dryness the residue was triturated with ethanol (30 mL) It was filtered the solution was concentrated in vacuo The residue was triturated with 2-propanol the precipitate was collected by suction filtration dried

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl (2E)-4-(dimethylamino)but-2-enoate (3.4 g, 23.7 mmol) was dissolved in methanol (25 mL). A solution of sodium hydroxide (0.95 g, 23.7 mmol) in water (7 mL) was added, and the mixture was heated to 50° C. for 1 h. The pH was then adjusted to 2 with conc. hydrochloric acid. The solution was concentrated to dryness, and the residue was triturated with ethanol (30 mL). It was filtered, and the solution was concentrated in vacuo. The residue was triturated with 2-propanol, and the precipitate was collected by suction filtration and dried to yield 2.00 g (51%) of the title compound. The solution was concentrated to dryness the residue was triturated with ethanol (30 mL) It was filtered the solution was concentrated in vacuo The residue was triturated with 2-propanol the precipitate was collected by suction filtration dried

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

実験手順: A sodium hydroxide solution (3.35 g in 25 ml of water, 0.084 moles) is added dropwise to a solution of 12 g methyl 4-dimethylaminocrotonate (0.084 moles) in 100 ml methyl alcohol at room temperature. The reaction mixture is heated to 40–45° C. for 1 hour then cooled to room temperature. The pH is adjusted to about 1˜2 with 5 N HCl. The mixture was concentrated to a thick oil, which is triturated with dehydrated alcohol to form a solid. The solid by-product is filtered and the filtrate is evaporated to an oil, which is triturated with isopropyl alcohol to afford 7.0 g of white solid product. Yield is 50% with the purity 86.3% by GC-MS. The reaction mixture is heated to 40–45° C. for 1 hour The mixture was concentrated to a thick oil, which is triturated with dehydrated alcohol to form a solid The solid by-product is filtered the filtrate is evaporated to an oil, which is triturated with isopropyl alcohol

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

実験手順: A solution of sodium hydroxide (3.35 g, 0.0838 mol) in water (24 mL) is added to a stirred solution of methyl 4-dimethylaminocrotonate (12 g, 0.0838 mol) in methanol (100 mL). The reaction mixture is warmed to 40–45° C. for 1 hour then cooled to room temperature. Hydrochloric acid (5N) is added to bring the pH of the reaction mixture to 1–2. The reaction mixture is concentrated under reduced pressure to a thick oil. Ethanol (anhydrous, 100 mL) is added and the solid (sodium chloride) is removed by filtration. The filtrate is concentrated under reduced pressure and product precipitation is induced by addition of 2-propanol (50 mL) to afford a solid which is collected to give the desired product (7.0 g, 50%). GC-MS purity is 86%. 1HNMR is consistent with expected structure. The reaction mixture is warmed to 40–45° C. for 1 hour The reaction mixture is concentrated under reduced pressure to a thick oil Ethanol (anhydrous, 100 mL) is added the solid (sodium chloride) is removed by filtration The filtrate is concentrated under reduced pressure and product precipitation is induced by addition of 2-propanol (50 mL)

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

実験手順: Trithylamine (37.5 ml, 0.27 mol, 2.8 equiv) was dissolved in THF (100 ml), and dimethylamine hydrochloride (9.3 g, 0.114 mol, 1.2 equiv) was added. Methyl 4-bromocrotonate (20 g, 85% purity, 0.095 mol, 1.00 equiv) in 100 ml of THF was added drop-wise to the resulting solution at room temperature while stirring. The reaction mixture was allowed to react overnight at room temperature. The reaction mixture was filtered, and the filtrate was evaporated under reduced pressure to give yellow oil. The oil was dissolved in 50 ml of isopropanol, and hydrogen chloride was added until pH 2.0 was reached. The white solid was formed and filtered and dried to give 7.1 g product. MS (ESI) m/z: 563 (M+1). to react overnight at room temperature The reaction mixture was filtered the filtrate was evaporated under reduced pressure to give yellow oil The white solid was formed filtered dried