2-(4-羟基苯基)-3,3,3-三氟丙酸乙酯的合成研究

报道了以苯酚和三氟丙酮酸乙酯为起始原料,在温和条件下合成高产率的2-(4-羟基苯基)-3,3,3-三氟丙酸乙酯的一条新途径.该途径包括无水碳酸钾催化的苯酚与三氟丙酮酸乙酯间的亲电取代反应、由此形成的产物的选择性侧连羟基的氯代反应和随后的硼氢化钠还原反应.

Facile Synthesis of Ethyl 2-(4-Hydroxyphenyl)-3,3,3-trifluoropropionate

This article describes a facile synthesis of ethyl 2-(4-hydroxyphenyl)-3,3,3-trifluoropropionate from ethyl trifluoropyruvate. Reaction of phenol with ethyl trifluoropyruvate was carried out in the presence of a catalytic amount of anhydrous potassium carbonate, and went smoothly at room temperature to afford ethyl 2-(4-hydroxyphenyl)-2-hydroxy- 3,3,3-trifluoropropionate (2) in high yield. Compound 2 was then converted into ethyl 2-chloro-(4-hydroxyphenyl)-3,3,3-trifluoropropionate (6) in good yield by selective chlorination with thionyl chloride and pyridine. Subsequent reduction of compound 6 with sodium borohydride was done in tetrahydrofuran at room temperature, yielding ethyl 2-(4-hydroxyphenyl)-3,3,3-trifluoropropionate in excellent yield.