Heptane → 3-(2-Chloro-4-methoxy-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol

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Reaction Steps

To a solution of 2-(2-chloro-4-methoxy-phenyl)-1-(2-chloro-pyridin-4-yl)-propan-1-on (14.75 g, 0.0475 mol) in tetrahydrofuran (900 ml) was added a solution of (trifluoromethyl)-trimethylsilane (14.89 g, 0.104 mol) in tetrahydrofuran (100 ml) at 0° C. (duration: 5 min.). Tetramethylammonium fluoride trihydrate 1M in THF (4.76 ml, 4.76 mmol) was added and the mixture was stirred at r.t. for 3 h. A second portion of Tetramethylammonium fluoride trihydrate 1M in THF (4.76 ml, 4.47 mmol) was added and the mixture was stirred at r.t. for 1 h. The mixture was poured in ice water and extracted twice with AcOEt. The organic phases were washed with saturated aqueous NaHCO3 solution and brine, dried over MgSO4, filtered and concentrated to give an oil, which solidified over night. The residue was treated with heptane, filtered off and dried to give the title compound (13.85 g) as a light yellow crystalline product. MS (m/e, ISP neg. ion)=378.4 [M−H+].

Provenance & Evidence