Imidazole → 4'-{[Tert-butyl(dimethyl)silyl]oxy}-2',6'-dimethylbiphenyl-3-carbaldehyde

Participants

Reaction Steps

To a solution of 4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde (9.0 g, 39.8 mmol) and imidazole (2.98 g, 43.8 mmol) in N,N-dimethylformamide (100 mL) was added tert-butyldimethylchlorosilane (6.6 g, 43.8 mmol) at room temperature with stirring, and the mixture was stirred at room temperature for 4 hrs. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1) to give the title compound (10.5 g, yield 77%) as a yellow oil.

Provenance & Evidence