Hydrochloric Acid → 2-[4-(tert-Butyldimethylsilyoxy)phenyl]-1-cyclohexyl-5-(1H-tetrazol-5-yl)-1H-benzimidazole

Participants

Reaction Conditions

Reaction Steps

Trimethylaluminum (20 mL of a 2.0 M solution in toluene, 0.040 mol) was added to a dry flask. Azidotrimethylsilane (5.3 mL, 0.040 mol) and compound 20 were added. The solution was stirred for 18 h at an oil bath temperature of 95° C. The solution was cooled and poured into a mixture of ethyl acetate and ice. The mixture was carefully acidified with dilute hydrochloric acid (caution-done in hood, hydrazoic acid liberated) to precipitate compound 21. The compound was crystallized from ethyl acetate—hexanes to afford 21 as a pinkish solid (4.13 g, 87%).

Provenance & Evidence