Potassium Iodide → 3-{3-[2,2,2-Trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-propan-1-ol

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Reaction Conditions

Reaction Steps

1.12 g (2.9 mmol) of 3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenol (example 5) in 20 ml of acetone were treated with 0.51 mL (5.9 mmol) of 3-bromo-1-propanol in the presence of 1.9 g (5.9 mmol) Cs2CO3 and 245 mg (1.5 mmol) of potassium iodide. The reaction mixture was stirred at 50° C. overnight, filtered and evaporated. The crude product was redissolved in EtOAc and a 1M KHSO4 solution, the phases were separated and the inorganic one extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and the solvent was evaporated. Column chromatography on silica gel yielded 1.1 g (84%) of 3-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-propan-1-ol as a colorless liquid, MS: 438 (M)+.

Provenance & Evidence