反应详情

To a solution of 4-cyclohexenylaniline (3,40 g, 0.023 mol) and methyl 4-formylbenzoate (3.77 g, 0.023 mol) in DCM (50 ml) and methanol (15 ml) was added a catalytic amount of acetic acid. After stirring the solution for 3 hours, Na(OAc)3BH (24 g, 0.115 mol) was added. The reaction was allowed to stir at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with aqueous sodium bicarbonate (3×), brine (2×), dried over magnesium sulphate, filtered, and concentrated to give an orange solid. The crude product was introduced into a column of silica gel and eluted with ethyl acetate:hexane (5:95) to give 4-[(4-cyclohex-1-enylphenylamino)methyl]benzoic acid methyl ester (5 g, 0.015 mol).

1. stirringto stir at room temperature for 16 hours
2. washwashed with aqueous sodium bicarbonate (3×), brine (2×)
3. dry with materialdried over magnesium sulphate
4. filtrationfiltered
5. concentrationconcentrated
6. customto give an orange solid
7. washeluted with ethyl acetate:hexane (5:95)