2,6-Lutidine → 3,3,3-Trifluoropropyl trifluoromethanesulfonate

Participants

Reaction Steps

To a cold (−25° C.), stirred solution of 2,6-lutidine (18.38 mL, 158 mmol) in DCM (120 mL) was added Tf2O (24.88 mL, 147 mmol) over 3 min, and the mixture was stirred for 5 min. To the reaction mixture was added 3,3,3-trifluoropropan-1-ol (12 g, 105 mmol) over an interval of 3 min. After 2 hour, the reaction mixture was warmed to room temperature and stirred for 1 hour. The reaction mixture was concentrated to half its volume, then purified by loading directly on a silica gel column (330 g ISCO). The product was eluted with DCM to afford Preparation 1A (13.74 g, 53%) as a colorless oil.

Provenance & Evidence