Water → 5-Quinolyl trifluoromethanesulfonate

Participants

Reaction Conditions

Reaction Steps

A solution of 5-hydroxy-quinoline (8 g, 55 mmol) and K2CO3 (15.2 g, 110 mmol) in anhydrous pyridine (60 mL) under nitrogen was cooled to −20° C. Tf2O (13.97 mL, 83 mmol) was added drop-wise via syringe. The reaction mixture was stirred 1 hour at −20° C. then warmed to 0° C. for 1 hour then stirred at ambient temperature for 48 hours. The reaction mixture was then poured into H2O (200 mL) and extracted in CH2Cl2 (2×200 mL). The aqueous layer was acidified with 1 N HCl (100 mL) and back extracted with CH2Cl2 (2×200 mL). The organic fractions were dried over Na2SO4, concentrated and purified by column chromatography (40% EtOAc/Hexanes) affording 13.97 g (90%) of the product as a pink oil: MS EI m/e 277 (M+).

Provenance & Evidence