Pyridine → (R)-6-(4-methyl-2-oxooxazolidin-4-yl)naphthalen-2-yl trifluoromethanesulfonate

Participants

Reaction Steps

Trifluoromethanesulfonic anhydride (0.144 mL, 0.000859 mol) was slowly added to a solution containing (R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (190 mg, 0.00078 mol), pyridine (2 mL, 0.02 mol), and methylene chloride (2 mL, 0.03 mol) at 0° C. After stirring overnight TLC showed complete reaction. After concentration, the crude was purified by chromatography using a 0-100% EtOAc/hexane gradient to give (R)-6-(4-methyl-2-oxooxazolidin-4-yl)naphthalen-2-yl trifluoromethanesulfonate as a yellow gel (259 mg, 88%). 1H NMR (400 MHz, CDCl3-d) δ=7.95 (s, 1H), 7.94-7.89 (m, 2H), 7.77 (d, J=1.9 Hz, 1H), 7.59 (dd, J=1.6, 8.6 Hz, 1H), 7.42 (d, J=9.0 Hz, 1H), 4.48 (d, J=8.4 Hz, 1H), 4.43 (d, J=8.4 Hz, 1H), 1.88 (s, 3H).

Provenance & Evidence