反应详情

To a solution of 4-[(4-butylphenyl)ethynyl]benzaldehyde (334 mg, 1.27 mmol, intermediate which may be obtained according to methods disclosed in EP03103780.7) and hexylamine (Aldrich, 98 μL, 1.53 mmol) in DCE (15.00 mL) was added acetic acid (110 mL) and sodium triacetoxyborohydride (405 mg, 1.91 mmol) and the resulting mixture was stirred at rt for 3 hrs. The reaction mixture was then diluted with DCM and washed with a saturated aqueous solution of NaHCO3 and brine. The organic layer was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by flash chromatography on silicagel (DCM, DCM/MeOH/NH4OH 98:2:1 then 95:5:1) to give 144 mg (32%) of the title compound. HPLC, Rt: 4.59 min (purity: 98.7%). 1H NMR (CD3Cl3) δ: 0.87 (t, J=6.9 Hz, 3H), 0.91 (t, J=7.3 Hz, 3H), 1.28-1.64 (m, 13H), 2.6 (t, J=7.3 Hz, 4H), 3.78 (s, 2H), 7.14 (d, J=8.1 Hz, 2H), 7.28 (d, J=8.3 Hz, 2H), 7.42 (d, J=8.3 Hz, 2H), 7.47 (d, J=8.1 Hz, 2H).

1. washwashed with a saturated aqueous solution of NaHCO3 and brine
2. dry with materialThe organic layer was dried over MgSO4
3. customthe solvents were removed under reduced pressure
4. customThe crude product was purified by flash chromatography on silicagel (DCM, DCM/MeOH/NH4OH 98:2:1