Imidazole → 8-(Tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

8-Hydroxyquinoline-2-carbaldehyde (5.00 g, 28.9 mmol) and imidazole (4.32 g, 63.5 mmol) was dissolved in dichloromethane (50 mL) under an atmosphere of dry N2. The reaction mixture was then cooled to 0° C. and tert-butylchlorodimethylsilane (4.94 g, 31.8 mmol) was added. The reaction was stirred overnight at ambient temperature, and then partitioned between dichloromethane and water. The organic layer was washed with water and aqueous saturated NaHCO3, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification via flash chromatography (2:1 Hexanes/dichloromethane followed by 1:1 hexanes/dichloromethane) provided 6.50 g, 78% of the desired product as an oil.

Provenance & Evidence