Potassium Carbonate → HCID 67816134, compound

Participants

Reaction Steps

4-(5-Trifluoromethyl-1H-benzoimidazol-2-yl)-butan-1-ol (2.2 g, 0 mmol) was dissolved in N,N-dimethylformamide (25 ml). Potassium carbonate (1.47 g, 10.65 mmol) was added, and the reaction stirred at RT for 1 h. SEM-Cl (1.66 ml, 9.37 mmol) was added dropwise, and the reaction stirred at RT for 3 h. An additional amount of SEM-Cl (0.50 ml, 2.81 mmol) was added dropwise, and the reaction stirred for a further 1 h. The reaction mixture was filtered, then concentrated under reduced pressure. The residue was redissolved in EtOAc (30 ml), and washed with water (3×30 ml, some NaCl added to aid separation). The organic layer was then dried (MgSO4) and concentrated to afford a red oil. The crude material was purified by biotage FCC, eluting with 18-100% EtOAc in heptane to afford 511.1 mg (15.4%) of 4-[5-Trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-butan-1-ol (regioisomer 1) and 738.6 mg (22.3%) of 4-[6-Trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-butan-1-ol (regioisomer 2) as yellow oils. Regioisomers was arbitrarily assigned.

Provenance & Evidence