4-Iodo-1-tritylimidazole → (2,5-Dimethylthien-3-yl)-1-trityl-imidazol-4-yl-methanol

Participants

Reaction Steps

To a solution of N-trityl-4-iodo-imidazole (11.8 g, 27 mmol) in dry CH2Cl2 (200 mL) was added EtMgBr (11.0 mL, 3.0M in Et2O). After complete halogen-metal exchange this solution was cannulated into a solution of 2,5-dimethylthiophene-3-carboxaldehyde (3.5 g, 25 mmol) in 50 mL of CH2Cl2. The reaction mixture was stirred at room temperature for 1 hr and then quenched with aqueous NH4Cl. The mixture was transferred to a separatory funnel and the aqueous layer was extracted with a second portion of CH2Cl2. The combined extracts were dried (MgSO4) and filtered. The solvent was evaporated in vacuo to give a thick syrup which was triturated with Et2O to give a solid which was recrystallized from acetone to give (2,5-dimethylthien-3-yl)-1-trityl-imidazol-4-yl-methanol, A5. 1H NMR (CDCl3) supported the assigned structure. ##STR46##

Provenance & Evidence