4-Iodo-1-tritylimidazole → HCID 10717796, compound

Participants

Reaction Steps

To a solution of N-trityl-4-iodo-imidazole (11.8 g, 27 mmol) in dry CH2Cl2 (75 mL) was added EtMgBr (10.0 mL, 3.0M in Et2O), and the solution was stirred for 3 hrs. Then a solution of 4-methylthiophene-3-carboxaldehyde (3.3 g, 27 mmol) in CH2Cl2 (25 mL) was added. The reaction mixture was stirred at room temperature overnight and then was 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 washed with a small portion of water, dried (Na2SO4), 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 with charcoal treatment from EtOAc to give (4-methylthien-3-yl)-1-trityl-imidazol-4-yl-methanol, B2. 1H NMR (CDCl3) supported the assigned structure. ##STR39##

Provenance & Evidence