2-Substituted-3-arylmethanone-6-(5-methyl-2-phenyl-4-ethoxyoxazole)benzofuran compound
A technology of ethoxy oxazole and benzofuran, applied in organic chemistry, organic active ingredients, antibacterial drugs, etc., can solve problems such as toxic and side effects, and achieve excellent antibacterial activity
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Embodiment 1
[0045] Synthesis of 4-(benzyloxy)-2-hydroxybenzaldehyde I ( Figure 4 ): Dissolve 2,4-dihydroxybenzaldehyde (100mg, 0.72mmol) in acetonitrile (15ml), then add potassium iodide (179.3mg, 1.08mmol) and sodium bicarbonate (90.7mg, 1.08mmol), then drop slowly Add benzyl chloride (100ul, 0.87mmol) and reflux for 12 hours. After the reaction was completed, it was quenched with water, extracted with ethyl acetate, the organic phases were combined, washed three times with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10 : 1) 110 mg of 4-(benzyloxy)-2-hydroxybenzaldehyde was obtained (colorless solid, yield 67%). 1 HNMR (CDCl 3 ; 300MHz), δ5.12(s, 2H, O CH 2 Ph) 6.40-6.64 (m, 2H, ArH), 7.41-7.43 (m, 6H, ArH), 9.73 (s, 1H, CHO), 11.44 (brs, 1H, OH).
Embodiment 2
[0047] (E)-5-(Benzyloxy)-2-(4-methoxystyryl)phenol II 1 Synthesis( Figure 4 ): under nitrogen atmosphere, add zinc powder (1.4g, 22mmol) in anhydrous tetrahydrofuran (20ml), then lower the temperature of the reaction system to -5~0°C, add titanium tetrachloride dropwise at this temperature (1.2ml, 11mmol), after the addition, the temperature of the reaction system was raised to room temperature, stirred for half an hour, and then refluxed for 2.5 hours. After the reflux, the temperature of the reaction system was lowered to -5~0°C again, and 4-(benzyloxy)-2-hydroxybenzaldehyde (1g, 4.4mmol) and p-methoxybenzaldehyde (721mg, 5.3mmol) of tetrahydrofuran solution, refluxed for 2 hours after dropping. After the reaction was completed, the reaction was quenched with 10% aqueous sodium bicarbonate solution, then extracted with dichloromethane, the organic phases were combined, washed three times with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced...
Embodiment 3
[0049] 6-(Benzyloxy)-2-(4-methoxyphenyl)benzofuran III 1 Synthesis( Figure 4 ): Dissolve (E)-5-(benzyloxy-2-(4-methoxystyryl)phenol (280mg, 0.84mmol) in tetrahydrofuran (15ml), add anhydrous potassium carbonate (695mg, 5.04 mmol), after stirring for 10 minutes, add iodine (1.28g, 5.04mmol), and stir at room temperature for 12 hours.After the reaction finished, quench the reaction with saturated aqueous sodium bicarbonate solution, then add dropwise saturated aqueous sodium bisulfite solution to remove The remaining iodine was extracted with ethyl acetate, the organic phases were combined, washed three times with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) 150 mg of 6-(benzyloxy)-2-methoxybenzofuran was obtained (yellow solid, yield 54%). 1 HNMR (CDCl 3 ;300MHz), δ3.87(s, 3H, OCH 3 ), 5.14(s, 2H, O CH 2 Ph), 6.826(s, 1H, ArH), 6.889-6.91...
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