반응 #466036
ord-46fa2750f0dc4f3783f0d7e2c6ae51f3
반응 조건
상세 조건
See reaction.notes.procedure_details.
후처리
- 1추출The mixture was extracted with ethyl acetate (4×150 mL)
- 2건조The combined organic layers were dried over magnesium sulfate
- 3기타The solvent was removed in vacuo
- 4기타the residue was chromatographed (silica, 20-30% ethyl acetate in hexanes)
실험 절차
To a solution of 2-methyl-3,5-dinitrobenzofuran (4.4 g, 19.8 mmol) in ethyl acetate (250 mL) was added stannous chloride (dihydrate, 8.99 g, 39.8 mmol). The mixture was stirred at room temperature for 70 hours. Water (100 mL) and 1N NaOH (100 mL) were added. The mixture was extracted with ethyl acetate (4×150 mL). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo and the residue was chromatographed (silica, 20-30% ethyl acetate in hexanes) to give 2-methyl-3-nitro-5-benzofuranamine as a yellow solid (1.71 g, 45%): 1H-NMR (270 MHz, CDCl3) δ 7.38 (d, 1H, J=2.8 Hz), 7.25 (d, 1H, J=8.8 Hz), 6.72 (dd, 1H, J=8.8, 2.8 Hz), 2.87 (s, 3H); HPLC (Method A) tR=1.36 min.