4-phenyl-1-(triphenylmethyl)-1H-imidazole → (3-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorophenyl) (4-phenyl-1-trityl-1H-imidazol-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-phenyl-1-trityl-1H-imidazole (8.1) (1.37 g, 3.54 mmol) in 20 mL THF at 0° C., was added BuLi (1.6 M in hexanes, 2.66 mL, 4.25 mmol). The mixture was stirred at 0° C. for 30 min, then a solution of 3-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorobenzaldehyde (188.3) (1.00 g, 3.54 mmol) in 3 mL THF was added dropwise. The mixture was stirred at 0° C. for 5 min, was removed from the cooling bath and stirred 45 min, then was quenched with sat. NH4Cl. The mixture was diluted with EtOAc, washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient) to afford 1.75 g of Intermediate 448.1 as a white foam. LCMS (2 min gradient) RT=2.22 min, 669.28 (M+H)+.

Provenance & Evidence