Water → [2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetaldehyde

Participants

Reaction Steps

To a solution of 200 mg (0.512 mmol) 2-[2-(4-chloro-phenyl)-benzoimidazol-1-yl]-2-cyclohexyl-ethanol (Ex. 1, intermediate c) in 2 ml dichloromethane was added 1.59 ml (2.17 g, 0.768 mmol) 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin-periodinane; 15 wt % in dichloromethane). The reaction mixture was stirred for 2 h at room temperature and then poured onto 30 ml dichloromethane and 30 ml water. The aqueous layer were extracted again with 30 ml dichloromethane. The combined organic layers were washed with 30 ml brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by silica 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 product as a colorless solid (74%). MS (Turbo Spray): m/z=389.2 [M+H].

Provenance & Evidence