3-methoxybutan-1-ol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: A stirred solution of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (1.715 g, 6 mmoles; prepared according to Preparation 1B), triphenylphosphine (1.58 g, 6 mmoles), 3-methoxy-1-butanol (0.62 g, 6 mmoles) in dry tetrahydrofuran (50 ml) was treated dropwise with diethyl azodicarboxylate (1.1 g of 95% purity material, 6 mmoles). The solution was left to stir overnight. After evaporation of the solvent the residue was dissolved in methylene chloride. The solution was washed with 0.4N NaOH, water, dried and the solvent evaporated. The residue was chromatographed over deactivated silica using methylene chloride (100), methanol (2.5), ammonium hydroxide (0.5) solvent system. The appropriate fractions were combined and the solvent evaporated. The residue (1.7 g) was crystallized from toluene to yield 1.17 g (52%) of the title compound, m.p. 76°-78° C. The solution was left After evaporation of the solvent the residue was dissolved in methylene chloride The solution was washed with 0.4N NaOH, water dried the solvent evaporated The residue was chromatographed over deactivated silica the solvent evaporated The residue (1.7 g) was crystallized from toluene

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

実験手順: A stirred solution of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (1.715 g, 6 mmoles; prepared according to Preparation 1B), triphenylphosphine (1.58 g, 6 mmoles), 3-methoxy-1-butanol (0.62 g, 6 mmoles) in dry tetrahydrofuran (50 ml) was treated dropwise with diethyl azodicarboxylate (1.1 g of 95% purity material, 6 mmoles). The solution was left to stir overnight. After evaporation of the solvent the residue was dissolved in methylene chloride. The solution was washed with 0.4N NaOH, water, dried and the solvent evaporated. The residue was chromatographed over deactivated silica using methylene chloride (100), methanol (2.5), ammonium hydroxide (0.5) solvent system. The appropriate fractions were combined and the solvent evaporated. The residue (1.7 g) was crystallized from toluene to yield 1.17 g (52%) of the title compound, m.p. 76°-78° C. The solution was left After evaporation of the solvent the residue was dissolved in methylene chloride The solution was washed with 0.4N NaOH, water dried the solvent evaporated The residue was chromatographed over deactivated silica the solvent evaporated The residue (1.7 g) was crystallized from toluene

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

実験手順: To a dichloromethane (30 mL) mixture of 3-methoxy-1-butanol (3.12 g, 30.0 mmol) and triethylamine (4.62 mL, 33.0 mmol), was added methanesulfonyl chloride (4.62 mL, 33.0 mmol) while stirring on ice, and the mixture was stirred at room temperature for 30 minutes. To the mixture, were added water and ethyl acetate. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was then filtered, and the solvent in the filtrate was then distilled off under reduced pressure. the mixture was stirred at room temperature for 30 minutes After thoroughly shaking the mixture the organic layer was separated the organic layer was washed with brine dried over anhydrous magnesium sulfate The mixture was then filtered the solvent in the filtrate was then distilled off under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: To a dichloromethane (30 mL) mixture of 3-methoxy-1-butanol (3.12 g, 30.0 mmol) and triethylamine (4.62 mL, 33.0 mmol), was added methanesulfonyl chloride (4.62 mL, 33.0 mmol) while stirring on ice, and the mixture was stirred at room temperature for 30 minutes. To the mixture, were added water and ethyl acetate. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was then filtered, and the solvent in the filtrate was then distilled off under reduced pressure. the mixture was stirred at room temperature for 30 minutes After thoroughly shaking the mixture the organic layer was separated the organic layer was washed with brine dried over anhydrous magnesium sulfate The mixture was then filtered the solvent in the filtrate was then distilled off under reduced pressure

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

実験手順: To a solution of 3-methoxybutane-1-ol (0.78 g, 7.5 mmol) and TEA (0.388 g, 3.8 mmol), in CH2Cl2 (15 mL) was added pentafluorobenzenesulfonyl chloride (0.79 g, 3.0 mmol). The solution was stirred at rt for 4 h. Saturated aqueous NaHCO3 (10 mL) was added to the solution and the mixture was stirred at rt for 30 min. The organics were extracted with CH2Cl2 (30 mL) and washed with 0.5 M HCl (2×20 mL) and saturated aqueous NaCl (1×20 mL). The organics were dried over Na2SO4 and concentrated to give a crude mixture. Silica gel chromatography (15% ethyl acetate in hexanes) yielded the desired product (0.39 g, 36%). 1H NMR (400 MHz CDCl3) δ 4.40 (m, 2H), 3.45 (m, 1H), 3.26 (s, 3H), 1.87 (m, 2H), 1.15 (d, 3H, J=6.1 Hz). Anal. Calcd. For C11H11F5O4S: C, 39.53; H, 3.32. Found: C, 39.83; H, 3.45. the mixture was stirred at rt for 30 min The organics were extracted with CH2Cl2 (30 mL) washed with 0.5 M HCl (2×20 mL) and saturated aqueous NaCl (1×20 mL) The organics were dried over Na2SO4 concentrated to give a crude mixture

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

実験手順: To a solution of 3-methoxybutane-1-ol (0.63 g, 6.0 mmol) and TEA (0.42 g, 4.1 mmol), in CH2Cl2 (5 mL) was added o-(trifluoromethyl)benzenesulfonyl chloride (0.50 g, 2.0 mmol). The solution was stirred at rt for 2 h. The reaction mixture was diluted with CH2Cl2 (15 mL) and washed with 1 M HCl (3×15 mL), saturated aqueous NaHCO3 (1×15 mL) and saturated aqueous NaCl (1×15 mL). The organics were dried over Na2SO4 and concentrated to give a crude mixture. Silica gel chromatography with ethyl acetate in hexanes yielded the desired product (0.34 g, 50%). 1H NMR (400 MHz CDCl3) δ 8.23 (m, 1H), 7.91 (m, 1H), 7.75 (m, 2H), 4.24 (m, 2H), 3.40 (m, 1H), 3.21 (s, 3H), 1.80 (m, 2H), 1.10 (d, 3H, J=6.2 Hz). Anal. Calcd. For C12H15F3O4S: C, 46.15; H, 4.84. Found: C, 46.30; H, 4.88. washed with 1 M HCl (3×15 mL), saturated aqueous NaHCO3 (1×15 mL) and saturated aqueous NaCl (1×15 mL) The organics were dried over Na2SO4 concentrated to give a crude mixture