Pyridine → 3-Butynyl triflate

Participants

Reaction Conditions

Reaction Steps

The compound was prepared following a procedure of Hummel et al. Liebigs Ann. Chem. 746, 211-213 (1971). Anhydrous pyridine (20.0 mL, 19.6 g, 0.248 mol) was added to a stirred solution of trifluoromethanesulfonic anhydride (70.0 g, 0.248 mol) in anhydrous CH2Cl2 (500 mL) at 0° C. over a dry nitrogen atmosphere in an oven-dried apparatus. A heavy white precipitate formed immediately, and the resulting slurry was stirred for 15 min at 0° C. A solution of 3-butyn-1-ol (16.6 g, 0.236 mol) in anhydrous CH2Cl2 (80 mL) was added dropwise at 0° C. The slurry was warmed to room temperature and stirred for 2 h. Pentane (1000 mL) was added and the precipitated salts were filtered and washed with pentane. Fractional distillation of the combined filtrates gave 39.9 g (84% yield) of 3-butynyl triflate as a colorless liquid:

Provenance & Evidence