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以3,4,5-三甲氧基甲苯(Ⅰ)为原料,经过Vilsmeier-Haack反应合成了6-甲基-2,3,4-三甲氧基苯甲醛(Ⅱ),收率94.1,Ⅱ经过Dakin反应得到2,3,4-三甲氧基-6-甲基苯酚(Ⅲ),收率96.2,用溴化苄对Ⅲ进行酚羟基保护得到2,3,4-三甲氧基-6-甲基苯基苄基醚(Ⅳ),收率95.0,Ⅳ在有机碱作用下发生溴代反应,得到6-甲基-5-溴-2,3,4-三甲氧基苯基苄基醚(Ⅴ),收率92.2,Ⅴ在超声波作用下制成格氏试剂(Ⅵ),再与4-溴-2-甲基-1-苯磺酰基-2-丁烯发生格氏偶联反应得到辅酶Q10的关键中间体3-(4-苯磺酰基-3-甲基-2-丁烯基)-4,5,6-三甲氧基-2-甲基苯基苄基醚(Ⅶ),收率72.0,五步反应总收率为57.1,产物经FTIR和1H NMR确定结构。
With 3,4,5-trimethoxytoluene (Ⅰ) as raw material, 6-methyl-2,3,4-trimethoxybenzaldehyde (Ⅱ) was synthesized by Vilsmeier-Haack reaction. Dakin reaction to obtain 2,3,4-trimethoxy-6-methylphenol (Ⅲ), the yield of 96.2, using benzyl bromide on the phenolic hydroxyl protection Ⅲ to give 2,3,4-trimethoxy-6-methyl Phenylbenzyl ether (Ⅳ), the yield of 95.0, Ⅳ under the action of organic base bromination reaction to give 6-methyl-5-bromo-2,3,4-trimethoxyphenyl benzyl ether ( Ⅴ) with a yield of 92.2. The Grignard reagent (Ⅵ) was prepared under Ⅴ ultrasonic wave and then Grignard coupling reaction with 4-bromo-2-methyl-1-phenylsulfonyl-2-butene gave the coenzyme The key intermediate of Q10 is 3- (4-benzenesulfonyl-3-methyl-2-butenyl) -4,5,6-trimethoxy-2-methylphenylbenzyl ether (VII) The rate of 72.0, the total yield of five-step reaction was 57.1, the product was confirmed by FTIR and 1H NMR structure.