Water → 3,4-dihydro-2H-chromen-2-ylmethyl trifluoromethanesulfonate

Participants

Reaction Conditions

Reaction Steps

Trifluoromethanesulfonic anhydride (19.6 g, 69.5 mmol) in DCM (15 mL) was added to a solution of the title compound from Step 1 (9.50 g, 57.9 mmol) in DCM (100 mL) and pyridine (11.0 g, 139 mmol) cooled to −5° C. The reaction was then stirred at 0° C. for 1 h. Water (150 mL) was added and the reaction was extracted with DCM (150 mL). The organic layer was washed with 1 M HCl (180 mL), water (100 mL), and NaHCO3 aqueous solution (100 mL). The organic phase was dried over Na2SO4, filtered and concentrated to give the title compound (13.5 g, 79%) as a pale-brown oil. 1H NMR (400 MHz, CDCl3): δ 7.12-7.04 (m, 2H), 6.90-6.83 (m, 2H), 4.66-4.61 (m, 2H), 4.36-4.31 (m, 1H), 2.96-2.79 (m, 2H), 2.09-2.03 (m, 1H), 1.95-1.84 (m, 1H). LCMS: 314 (M+NH4)+

Provenance & Evidence