Trifluoromethanesulfonic anhydride → 5-Methoxynaphthalen-1-yl trifluoromethanesulfonate

Participants

Reaction Steps

To a solution of 5-methoxynaphthalen-1-ol (above Step-1 intermediate) (19 g, 0.11 mol) in anhydrous dichloromethane (250 mL) at 0° C. was added, DIPEA (23 mL, 0.16 mol) and the mixture was stirred for 15 min. To this, Tf2O (21.7 mL, 0.13 mol) was added slowly at 0° C. and the reaction mixture was stirred for 1.5 h and then quenched slowly with water (100 mL). The aqueous layer was extracted with CH2Cl2 (4×100 mL) and the combined organic layer was washed with water (100 mL), brine (100 mL), dried and filtered. The solvent was then evaporated and the crude product was purified by column chromatography (5% EtOAc:Hexanes) to furnish the desired compound (28.5 g, 85%) as a white solid.

Provenance & Evidence