| 95% |
With potassium carbonate In propan-2-one for 18h; Reflux; |
4.1.5 (2R)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-yl (2E)-3-[2-(3,4-dimethoxyphenyl)-7-methoxy-1-benzofuran-4-yl]prop-2-enoate (7)
Salvianolic acid C (206mg, 0.419mmol) was placed into a boiling flask and dispersed in 15mL of acetone containing anhydrous potassium carbonate (1.16g, 8.374mmol). To the suspension 714.5μL (7.542mmol) of dimethyl sulfate was added, and the reaction mixture was stirred for 18h under reflux. After completing, acetone was removed by a rotary evaporator. The residue was suspended in saturated NH4Cl resolution (15mL) and then extracted with ethyl acetate (20mL×4). The organic layer was washed with brine, dried with anhydrous Na2SO4 and concentrated in vacuum. The obtained residue was further separated by silica gel chromatography using chroloform/methanol as the eluent to give pure compound 7 as a yellow foam (230mg, yield 95%). 1H NMR (CDCl3, 300MHz) δ 7.96 (d, 1H, J=15.9Hz), 7.53 (dd, 1H, J=8.4, 2.1Hz), 7.39 (m, 2H), 7.17 (s, 1H), 6.97 (d, 1H, J=8.4Hz), 6.82 (m, 4H), 6.50 (d, 1H, J=15.9Hz), 5.41 (m, 1H), 4.09 (s, 3H), 4.03 (s, 3H), 3.96 (s, 3H), 3.88 (s, 3H), 3.86 (s, 3H), 3.78 (s, 3H), 3.21-2.80 (m, 2H); 13C NMR (CDCl3, 75MHz) δ 170.5, 166.7, 157.6, 150.1, 149.2, 148.8, 148.8, 146.9, 144.1, 143.7, 130.7, 128.4, 125.8, 122.7, 121.4, 121.4, 118.5, 114.9, 112.5, 111.3, 111.2, 108.2, 106.6, 99.2, 73.1, 56.2, 56.2, 56.0, 55.8, 55.8, 52.4, 37.2. HR-MS (ESI) m/z: calcd. for C32H33O10 [M+H]+: 577.2079; found: 577.2068. |
| 92% |
With potassium carbonate Sonication; Reflux; |
7 (2R) - 3 - (3,4-dimethoxyphenyl) - 1-methoxy-1-oxopropan-2-yl (2E) - 3 - [2 - (3,4-dimethoxyphenyl) - 7-methoxy-1-benzofuran-4-yl] prop-2-enoate (7)
Accurate weighing Salvianolic acid C (206 mg, 0 . 419mmol) in the round bottom b neck flask, plus 15mLMe2CO ultrasonic dissolved, (quantity) that the accurate K2CO3(1.16g, 8 . 374mmol), Me2SO4(714.5 ml, 7 . 542mmol) salvianolic acid C in the sample solution is added, reflux reaction, and TLC (cyclohexane/ethyl acetate the 1 [...] 1) monitoring, basically disappear until the reaction raw materials. After the reaction terminates, the solvent evaporation to dryness, saturated NH4Cl aqueous solution (20 ml) dilution, using ethyl acetate (20 ml × 4) extraction, combined with the organic layer, the saturated salt water washing, MgSO4drying, concentrating under reduced pressure, the mixture, which is obtained by the sample. For gradient elution of the silica gel column (cyclohexane/ethyl acetate 10 the [...] 1, the 5 [...] 1v/v), to obtain a reaction product 7 (431 mg, yield 92%). |
| 92% |
With potassium carbonate Sonication; Reflux; |
7 (2R) - 3 - (3,4-dimethoxyphenyl) - 1-methoxy-1-oxopropan-2-yl (2E) - 3 - [2 - (3,4-dimethoxyphenyl) - 7-methoxy-1-benzofuran-4-yl] prop-2-enoate (7)
Accurate weighing Salvianolic acid C (206 mg, 0 . 419mmol) in the round bottom b neck flask, plus 15mLMe2CO ultrasonic dissolved, (quantity) that the accurate K2CO3(1.16g, 8 . 374mmol), Me2SO4(714.5 ml, 7 . 542mmol) salvianolic acid C in the sample solution is added, reflux reaction, and TLC (cyclohexane/ethyl acetate the 1 [...] 1) monitoring, basically disappear until the reaction raw materials. After the reaction terminates, the solvent evaporation to dryness, saturated NH4Cl aqueous solution (20 ml) dilution, using ethyl acetate (20 ml × 4) extraction, combined with the organic layer, the saturated salt water washing, MgSO4drying, concentrating under reduced pressure, the mixture, which is obtained by the sample. For gradient elution of the silica gel column (cyclohexane/ethyl acetate 10 the [...] 1, the 5 [...] 1v/v), to obtain a reaction product 7 (431 mg, yield 92%). |
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