Water → HCID 22995917, compound

Participants

Reaction Conditions

Reaction Steps

13.21 ml of triethylamine and 7 ml of methanesulfonyl chloride are successively added to a solution, cooled to 0° C. with an ice bath, of 13.8 g (30.53 mmol) of 2-trifluoromethanesulfonyloxy-8-(1′-hydroxy-2′-tert-butyldimethylsilyloxyethyl)quinoline in 300 ml of ethyl ether. The mixture is stirred for 30 min at 0° C. and then for 10 min at ambient temperature and is hydrolyzed by the addition of 300 ml of water. 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 dissolved in 200 ml of chloroform and 45 ml of diethylamine and the mixture is brought to reflux for 16 h. 200 ml of water are added and extraction is carried out with ethyl acetate (3×150 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 14 g of 2-trifluoromethane sulfonyloxy-8-(1-diethylamino-2-tert-butyldimethylsilyloxyethyl)quinoline in the form of a yellow oil. (Yield: 90%)

Provenance & Evidence