Aluminium lithium hydride → 2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclopropyl-ethanol

Participants

Reaction Steps

To an ice-cold suspension of 3.0 g (8.27 mmol) [2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclopropyl-acetic acid in 105 ml tetrahydrofuran were added in portions 0.47 g (12.4 mmol) lithium aluminium hydride. After removal of the cooling bath the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was poured onto 200 ml potassium sodium tartrate solution wan was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to give a yellow solid which was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane:ethyl acetate (100:0 to 50:50). The product containing fractions were pooled and evaporated until precipitation started. The suspension was filtered and washed with n-heptane to give the desired compound as an off-white solid (56%). MS (Turbo Spray): m/z=349.2 [M+H].

Provenance & Evidence