Ethyl Acetate → 2-[2-(4-Chloro-2-methyl-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol

Participants

Reaction Steps

To a solution of 0.94 g (2.244 mmol) [2-(4-chloro-2-methyl-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acid in 15 ml dry tetrahydrofuran was added 98 mg (2.356 mmol) lithium aluminum hydride at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 2 hours. The reaction mixture was poured on 50 ml 10% aqueous sodium potassium tartrate solution and 50 ml ethyl acetate. The layers were separated and the aqueous layers were extracted again with 50 ml ethyl acetate. The combined organic layers were washed with 50 ml brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 60:40) to give the title compound as a light yellow solid (57%). MS (Turbo Spray): m/z=405.4 [M+H].

Provenance & Evidence