反应详情

温度

60 °C

The resulting 5-benzyloxy-thiophene-2-carbaldehyde (171 mg) was dissolved in N,N-dimethylformamide (4 mL), pyridine (82 μl, 1.02 mmol) and hydroxylamine hydrochloride (65 mg, 0.94 mmol) were added thereto, followed by stirring for 30 minutes at 60° C., then, cooled on an ice bath. 1,1′-Carbonyldiimidazole (635 mg, 3.92 mmol) was added, the solution was warmed again to 60° C. and stirred for 35 minutes, triethylamine (272 μl, 1.96 mmol) was added, and the solution was further stirred for 30 minutes. The reaction mixture was cooled to room temperature, water was added, and the solution was extracted with ethyl acetate. The organic layer was sequentially washed with an aqueous solution of oxalic acid, an aqueous solution of saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate, and then, concentrated in vacuo. The resulting residue was purified by silica gel chromatography (hexane-ethyl acetate), and the title compound (30 mg, 0.14 mmol, 14%) was obtained.

1. temperaturecooled on an ice bath
2. temperaturethe solution was warmed again to 60° C.
3. stirringstirred for 35 minutes
4. stirringthe solution was further stirred for 30 minutes
5. temperatureThe reaction mixture was cooled to room temperature
6. extractionthe solution was extracted with ethyl acetate
7. washThe organic layer was sequentially washed with an aqueous solution of oxalic acid
8. dry with materialan aqueous solution of saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate
9. concentrationconcentrated in vacuo
10. customThe resulting residue was purified by silica gel chromatography (hexane-ethyl acetate)