合成路线 1（1. 合成：7567-63-7）
产率：87%
合成条件：Stage #1: With caesium carbonate In methanol for 16 h; Stage #2: With ammonium chloride In dichloromethane; water
实验步骤：（9）1,3,5-三乙炔基苯。 在氩气下向火焰干燥的烧瓶中加入（8）（2.39mmol，1当量），碳酸铯（4.78mmol，2当量）和甲醇（10mL）。 将反应搅拌16小时。 完成后，解决方案从不透明变为半透明。 真空除去甲醇，将固体在水和二氯甲烷之间分配。 用二氯甲烷（3×20mL）萃取水层。 用氯化铵水溶液（1.0M，2×20mL），水（2×20mL）和盐水（2×20mL）洗涤有机层。 用硫酸钠干燥有机层，过滤，并真空除去。 得到产物，为灰白色软晶体（2.09mmol），产率87％，熔点101-103℃.1H NMR（400MHz，CDCl3）δ7.57（s，3H），3.12（s，3H）。 13 C NMR（100MHz，CDCl 3）δ135.6,122.8,81.6,78.7。 MS（CI +）m / z 151 [M] +。
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合成路线 2（2. 合成：7567-63-7）
产率：92%
合成条件：With potassium hydroxide In toluene at 110℃; for 8 h;
实验步骤：一般程序：按照Sonogashira偶联方案修改程序。在氮气氛下，将1,3,5-三溴苯（31.5g，100mmol）溶解在无水三乙胺（250mL）中。将碘化亚铜（I）（191mg，1.0mmol），二氯双（二苯甲腈）钯（II）（192mg，0.5mmol）加入到搅拌的溶液中。滴加2-甲基-3-丁炔-2-醇（12.6g，150mmol）后，将反应混合物在氮气氛下回流12小时。在室温下，滤出形成的三乙胺氢碘酸盐沉淀，并用乙醚（3×50mL）洗涤。将合并的滤液用无水Na 2 SO 4干燥并蒸发，得到粗产物。在-20℃下将该粗产物在20mL乙醇中重结晶，得到2,2'，2“ - （苯-1,3,5-三基三（乙炔-2,1-二基））三基的白色晶体。 （丙-2-醇）（3）（30.8g，95％）。化合物3的水解通过在110℃下搅拌8小时，用KOH（19.2g）和甲苯150mL处理来进行。蒸发有机溶剂，用乙醚萃取残余物，用Na 2 SO 4干燥，减压除去溶剂，得到1,3,5-三乙炔苯4）（13.0g，92％），为无色针状结晶。熔点95.4-96.0℃; 1H NMR（300MHz，CDCl3，ppm）δ3.10（s，3H），7.57（s，3H）。
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