Water → (4-chloro-phenyl)-{4-[hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl]-1-methyl-1H-pyrrol-2-yl}methanone

Participants

Reaction Steps

To 4.4 g (0.01 mole) 4-iodo-1-tritylimidazole in 80 mL of CH2Cl2 was added dropwise 3.3 mL of 3.0 M ethylmagnesium bromide in Et2O. After stirring for 1 h, a solution of 1.0 g (0.004 mole) of 5-(4-chlorobenzoyl)-1-methyl-1H-pyrrole-3-carboxaldehyde in 10 mL of CH2Cl2 was added dropwise. The resulting reaction mixture was stirred for 2.5 h after which it was poured into water. The solid was filtered off through celite. The organics from the filtrate were separated off, washed with water, brine and dried (Na2SO4). The solvent was evaporated in vacuo to give 3.1 g of (4-chlorophenyl)-{4-[hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl]-1-methyl-1H-pyrrol-2yl}-methanone: CI-MS m/z=559 (M++H). 1HNMR (CDCl3) δ 7.7 (m, 5H) 7.4-7.0 (m, 16H); 6.5 (m, 1H); 3.75 (s, 3H).

Provenance & Evidence