methyl 4-[(E)-hydroxyiminomethyl]benzoate

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

実験手順: To a solution of methyl 4-[(E)-(hydroxyimino)methyl]benzoate (6.3 g, 39 mmol) in 2-methyltetrahydrofuran (60 mL) and of dimethyl acetamide (7 mL) was added a solution of HCl in dioxane (4.0 M, 195 uL, 0.78 mmol) and the mixture was cooled in an ice bath. NCS (5.48 g, 41.0 mmol) was added portionwise maintaining the internal temperature below 10 C. The mixture was stirred at 20 C for 30 min and then was cooled in an ice bath. MsCl (4.7 g, 41 mmol) was added followed by DIPEA (5.55 g, 43 mmol) dropwise maintaining the internal temperature below 10 C. The mixture was warmed to 20 C and stirred for 1 h. The reaction was partitioned between EtOAc and water and the organic layer was washed with water (3×), brine (1×), dried over MgSO4 and the solvent removed to give a colorless solid (5.52 g, 54% yld). the mixture was cooled in an ice bath maintaining the internal temperature below 10 C was cooled in an ice bath dropwise maintaining the internal temperature below 10 C The mixture was warmed to 20 C stirred for 1 h The reaction was partitioned between EtOAc and water the organic layer was washed with water (3×), brine (1×) dried over MgSO4 the solvent removed to give a colorless solid (5.52 g, 54% yld)

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

実験手順: To a solution of methyl 4-[(E)-(hydroxyimino)methyl]benzoate (6.3 g, 39 mmol) in 2-methyltetrahydrofuran (60 mL) and of dimethyl acetamide (7 mL) was added a solution of HCl in dioxane (4.0 M, 195 uL, 0.78 mmol) and the mixture was cooled in an ice bath. NCS (5.48 g, 41.0 mmol) was added portionwise maintaining the internal temperature below 10 C. The mixture was stirred at 20 C for 30 min and then was cooled in an ice bath. MsCl (4.7 g, 41 mmol) was added followed by DIPEA (5.55 g, 43 mmol) dropwise maintaining the internal temperature below 10 C. The mixture was warmed to 20 C and stirred for 1 h. The reaction was partitioned between EtOAc and water and the organic layer was washed with water (3×), brine (1×), dried over MgSO4 and the solvent removed to give a colorless solid (5.52 g, 54% yld). the mixture was cooled in an ice bath maintaining the internal temperature below 10 C was cooled in an ice bath dropwise maintaining the internal temperature below 10 C The mixture was warmed to 20 C stirred for 1 h The reaction was partitioned between EtOAc and water the organic layer was washed with water (3×), brine (1×) dried over MgSO4 the solvent removed to give a colorless solid (5.52 g, 54% yld)