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

Participants

Reaction Steps

To a solution of 8-hydroxyquinoline-2-carbaldehyde (15.0 g, 86.62 mmol) and imidazole (12.97 g, 190.6 mmol) in anhydrous CH2Cl2 (250 mL) at 0° C. was added tert-butylchlorodimethylsilane (14.36 g, 95.28 mmol). The mixture was allowed to warm slowly to ambient temperature over 16 hours and then partitioned between CH2Cl2 and water. The aqueous phase was extracted with CH2Cl2 and the combined organic phases were washed successively with saturated NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel pad filtration eluting with hexanes followed by 19:1 ethyl acetate/hexanes to provide 23.69 g (95%) of desired product as a dark yellow oil.

Provenance & Evidence