反应详情

Sulfur trioxide pyridine complex (240 mg, 1.5 mmol) was added to a solution of 3-[3-(5-isoquinolinylsulfonyloxy)-5-methylphenoxy]propanol (190 mg, 0.5 mmol), as prepared in the preceding step, N,N-diisopropylethylamine (0.2 mL, 1.6 mmol) and anhydrous dimethyl sulfoxide (0.1 mL, 1.4 mmol) in anhydrous dichloromethane (20 mL). The reaction mixture was stirred at ambient temperature for 1 hour and then quenched with 10% aqueous citric acid (30 mL). The mixture was extracted into dichloromethane (3×30 mL), and the dichloromethane solution was washed with 10% aqueous citric acid (30 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (3:1 ethyl acetate/dichloromethane) to give the title compound as a colorless oil (135 mg, 72%). 1H-NMR (300 MHz, CDCl3) δ 9.79 (s, 1H), 9.46 (s, 1H), 8.80 (d, J=6.2 Hz, 1H), 8.59 (d, J=5.8 Hz, 1H), 8.37 (d, J=7.5 Hz, 1H), 8.34 (d, J=8.3 Hz, 1H), 7.71 (t, J=7.7 Hz, 1H), 6.56 (s, 1H), 6.32 (s, 1H), 6.24 (s, 1H), 4.09 (t, J=6.0 Hz, 2H), 2.81 (t, J=6.0 Hz, 2H), 2.17 (s, 3H).

1. customquenched with 10% aqueous citric acid (30 mL)
2. extractionThe mixture was extracted into dichloromethane (3×30 mL)
3. washthe dichloromethane solution was washed with 10% aqueous citric acid (30 mL)
4. dry with materialdried over Na2SO4
5. customAfter removing the solvent in vacuo
6. customthe residue was purified by flash column chromatography (3:1 ethyl acetate/dichloromethane)