反应详情

To a solution of 2,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carbaldehyde (510 mg, 2.47 mmol) in anhydrous DCE (20 mL) was added n-hexylamine (392 μL, 2.97 mmol), acetic acid (212 μL) and sodium triacetoxyborohydride (786 mg, 3.71 mmol) and the resulting mixture was stirred at rt for 3 hrs. The reaction mixture was 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. Purification by flash chromatography on silicagel (EtOAc/c-Hex (20/80)) gave 627 mg (87%) of the title compound. HPLC, Rt: 2.70 min purity: 86.4% ). 1H NMR (CDCl3) δ: 0.85 (t, J=6.8 Hz, 3H), 1.28 (m, 6H), 1.48 (m, 2H), 1.70 (s, 6H), 2.41 (m, 1H), 2.58 (t, J=7.3 Hz, 2H), 3.74 (s, 2H), 6.90 (d, J=8.5 Hz, 1H), 7.53 (dd, J=8.5, 2.3 Hz, 1H), 7.86 (d, J=2.1 Hz, 1H).

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. customPurification by flash chromatography on silicagel (EtOAc/c-Hex (20/80))