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Preparation of (R)-3,5-bis(tri?uoromethyl)phenyl ethanol by kinetic resolution

WANG Liang,XU Gang,YANG Lirong   

  1. Department of Chemical and Biological Engineering,Zhejiang University,Hangzhou 310027,Zhejiang,China
  • Online:2013-11-05 Published:2013-11-05

动力学拆分制备(R)-3,5-双三氟甲基苯乙醇

王 亮,徐 刚,杨立荣   

  1. 浙江大学化学工程与生物工程学系,浙江 杭州 310027

Abstract: (R,S)-3,5-bis(tri?uoromethyl)phenyl ethanol was prepared by reduction of 3,5-bis (tri?uoromethyl) acetophenone with the NaBH4 as reducing agent. Two efficient and highly selective lipases,Novozym 435 and Rhizopus arrhizus,were screened with (R,S)-3,5- bis(tri?uoromethyl)phenyl ethanol as substrate. Rhizopus arrhizus was selected as our experimental lipase and the factors which affected kinetic resolution were studied. When n-hexane was selected as solvent,optically pure (R)-3,5- bis (trifluoromethyl) phenyl ethyl acetate could be obtained after 30 min at 40 ℃. After post-processing,we obtained (R)-3,5-bis (trifluoromethyl) phenyl ethyl with the e.e. value of 100%.

Key words: (R)-3,5-bis(tri?uoromethyl)phenyl ethanol, kinetic resolution, 3,5-bis(tri?uoromethyl) acetophenone

摘要: 通过动力学拆分方法,由3,5-双三氟甲基苯乙酮出发,经过NaBH4还原,制备得到高纯度消旋化的(R,S)-3,5-双三氟甲基苯乙醇。经过筛选得到2种高效高选择性动力学拆分(R,S)-3,5-双三氟甲基苯乙醇的脂肪酶:Novozym 435和Rhizopus arrhizus。以Rhizopus arrhizus作为实验脂肪酶,考察了影响其动力学拆分的因素,包括溶剂、反应温度和底物浓度,获得最佳的反应条件为:正己烷作为溶剂,40 ℃下反应,底物浓度为100 mmol/L。在最佳的条件下,以乙酸乙烯酯作为酰基供体进行动力学拆分反应,经过后期的分离纯化,成功制备得到了e.e.值接近100%的(R)-3,5-双三氟甲基苯乙醇。

关键词: (R)-3, 5-双三氟甲基苯乙醇, 动力学拆分, 3, 5-双三氟甲基苯乙酮。

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