3-{[tert-Butyl(dimethyl)silyl]oxy}-5-ethyl-2-fluorobenzaldehyde → (3-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorophenyl)(5,6-dimethyl-1-trityl-1H-benzo[d]imidazol-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of intermediate 415.1 (100 mg, 0.257 mmol) in 2 mL THF at 0° C., was added BuLi (1.6 M in hexanes, 193 μL, 0.309 mmol). The mixture was stirred at 0° C. for 20 min, then a solution of 3-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorobenzaldehyde (188.3) (72.6 mg, 0.257 mmol) in 0.6 mL THF was added. The mixture was removed from the ice bath and stirred 70 min, then was quenched with sat. NH4Cl. The mixture was diluted with EtOAc, washed with H2O and brine, dried (Na2SO4) and concentrated. The crude residue was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient) to afford 115 mg of intermediate 415.2. LCMS (2 min gradient) RT=2.24 min, 671.13 (M+H)+.

Provenance & Evidence