Imidazole → HCID 22995910, compound

Participants

Reaction Steps

A solution of 12 g (35 mmol) of 2-trifluoromethanesulfonyloxy-8-(1,2-dihydroxyethyl)quinoline, of 5.33 g (78.3 mmol) of imidazole and of 5.63 g of tert-butyldimethylsilyl chloride in 280 ml of DMF is stirred at ambient temperature for 16 h. 800 ml of water are added and extraction is carried out with ethyl acetate (3×250 ml). The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by silica chromatographic column (eluent: cyclohexane/ethyl acetate 8/2) to provide 13.8 g of 2-trifluoromethanesulfonyloxy-8-(1-hydroxy-2-tert-butyldimethylsilyloxyethyl)quinoline in the form of a yellow oil. (Yield: 91%)

Provenance & Evidence