反应详情

To a solution of 2-fluoro-N1,N1-di-n-hexyl benzene-1,4-diamine (0.58 g, 1.97 mmol) in CH2Cl2 (20 mL) was added trimethylaluminum (9.9 mL, 19.8 mmol, 2 M in heptane) slowly at rt. The reaction mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (341 mg, 2.17 mmol) in CH2Cl2 (5 mL). The reaction mixture was stirred at rt for 3 days, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (100 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as pale yellow oil (500 mg, 63%). The compound was characterized by the following spectroscopic data:

1. stirringThe reaction mixture was stirred at rt for 3 days
2. customquenched with saturated NH4Cl aqueous solution
3. extractionextracted with CH2Cl2 (100 mL×3)
4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
5. concentrationconcentrated in vacuo
6. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)