反应详情

温度

70 °C

To a solution of 6-({4-[(4-methoxyphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one (416 mg; 1.01 mmol) in anhydrous DCE (15 mL) were added hexanal (Aldrich, 181 μl; 1.51 mmol), sodium triacetoxyborohydride (426 mg, 2.01 mmol) and acetic acid (115 μl). The resulting mixture was heated at 70° C. under nitrogen atmosphere for 24 h and poured into a saturated aqueous solution of NaHCO3. The aqueous layer was extracted with DCM (twice) and combined organic layers were washed with brine, dried over magnesium sulfate, filtrated and concentrated. Purification by flash chromatography on silica gel (EtOAc/c-Hex 5:95 then 10:90) gave 520 mg of the title compound (quantitative). HPLC, Rt : 5.82 min (purity: 99.9%). LC/MS, M+(ESI): 498.7. 1H NMR (CDCl3) δ: 7.43 (d, J=8.9 Hz, 4H), 7.21 (s, 1H), 7.16 (d, J=8.1 Hz, 2H), 6.74-6.86 (m, 4H), 4.48 (s, 2H), 3.80 (s, 3H), 3.34 (t, J=7.8 Hz, 2H), 1.68 (s, 6H), 1.61 (m, 2H), 1.27 (s, 6H), 0.86 (m, 3H).

1. extractionThe aqueous layer was extracted with DCM (twice) and
2. washwere washed with brine
3. dry with materialdried over magnesium sulfate
4. filtrationfiltrated
5. concentrationconcentrated
6. customPurification by flash chromatography on silica gel (EtOAc/c-Hex 5:95