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CAS No. : | 4225-35-8 | MDL No. : | MFCD12079199 |
Formula : | C10H10O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 194.18 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With potassium hydroxide In methanol; water at 20℃; for 2h; | General Procedure H: Synthesis of Aurones (GP-H) General procedure: To a stirred solution of benzofuranone (1.0 equiv) in MeOH (20 mL) was added the corresponding hydroxybenzaldehyde (1.2 equiv) followed by the addition of KOH (6.5 equiv) in H2O (20 mL). The reaction mixture was stirred at room temperature for 2 h and then poured into H2O (100 mL). The resulting suspension was neutralized to pH 7 with 3 M HCl and extracted with CHCl3 (3 × 50 mL). The combined organic layer was washed with H2O (3 × 50 mL), brine (3 × 50 mL), dried over anhydrous MgSO4, filtered and evaporated to dryness under reduced pressure. The crude residue was purified by flash column chromatography over silica and recrystallized from MeOH to afford the corresponding aurones. 4,6-Dimethoxy-3’-hydroxyaurone (134). A mixture of benzofuranone 21 (1.01 g, 5.20 mmol), benzaldehyde 131 (760 mg, 6.22 mmol) and KOH (1.50 g, 26.6 mmol) in MeOH/H2O (1:1, 40 mL) was reacted according to GP-H. The crude residue was purified by flash column chromatography (SiO2, PE/EtOAc; 1:1) and recrystallized from MeOH to afford aurone 134 (1.21 g, 78%) as a bright yellow powdery solid. |
76% | With potassium hydroxide In methanol; water Reflux; | |
With sodium hydroxide |
With hydrogenchloride; acetic acid | ||
With potassium hydroxide In water Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In ethanol; water at 80℃; | Preparation of (2Z)-4,6-dimethoxy-2-[(1 -methyl-2-phenyl-1 H-indol-3- yl)methylene]benzofuran-3(2H)-one: To a mixture of 1-methyl-2-phenyl-1 H-indole-3-carbaldehyde (471 mg, 2.002 mmol), 4,6- dimethoxybenzofuran-3(2H)-one (389 mg, 2.002 mmol) and ethanol (30 ml_) was added 2 drops of concentrated hydrochloric acid. All solids dissolve to give a deep maroon solution, which slowly lightens and precipitates a solid, while heated by an oil bath at 80 0C. Stirred overnight. Reaction mixture cooled and the solid collected washed with ethanol and air dried to give an orange brown solid, (2Z)-4,6-dimethoxy-2-[(1-methyl-2-phenyl-1 H-indol-3- yl)methylene]benzofuran-3(2H)-one (699 mg, 1.699 mmol, 85 % yield), mp 257-8. MS (m/z) 414.2 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With potassium hydroxide In methanol; water Reflux; | |
91% | With potassium hydroxide In methanol; water at 25℃; for 2h; | 7 5.1.7 (Z)-2-(2,4-Dimethoxybenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one (38) To a solution of 4,6-dimethoxybenzofuran-3(2H)-one (245 mg, 2.06 mmol) in MeOH (30 mL) were added an aqueous solution of KOH (50%, 2 mL) and 2,4-dimethoxybenzaldehyde (315 mg, 3.09 mmol), and the mixture was stirred at room temperature for 2 h. The solid was then filtered, washed with cold MeOH and dried. The crude product was recrystallized from MeOH to afford 38 (394 mg, 91%) as a pale yellow solid. 1H NMR (CDCl3) δ 8.19 (d, 1H, J = 8.7 Hz), 7.27 (s, 1H), 6.57 (dd, 1H, J = 8.7 Hz, J = 2.3 Hz), 6.45 (d, 1H, J = 2.3 Hz), 6.36 (d, 1H, J = 1.7 Hz), 6.11 (d, 1H, J = 1.7 Hz), 3.94 (s, 3H), 3.90 (s, 3H), 3.87 (s, 3H), 3.86 (s, 3H). 13C NMR (CDCl3) δ 180.6, 168.5, 168.4, 162.2, 160.1, 159.2, 146.8, 132.8, 114.6, 105.6, 105.5, 105.3, 97.9, 93.7, 89.0, 56.1, 56.0, 55.5, 55.4. IR (ATR) υ 1591, 1566, 1426, 1318, 1240, 1208, 1157, 1088, 1042, 1030, 945, 916, 883, 845, 806, 783, 696, 675, 550, 507 cm-1. HRMS (ESI) calc. for C19H19O6 [M + H]+ 343.1176, found 343.1170. |