Pyridine → 2-formyl-3-methyl-5-(tetrahydro-2H-pyran-2-yloxy)phenyl trifluoromethanesulfonate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-hydroxy-6-methyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (8.70 g, 36.8 mmol) and pyridine (14.56 g, 184.1 mmol) in dichloromethane (40 mL) was slowly added Tf2O (15.58 g, 55.2 mol) at −10 to 0° C. The mixture was stirred at 0° C. for 3 hours. The mixture was diluted with cold brine and extracted with 50% EtOAc/hexane. The organic extracts were washed with brine, dried and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (EtOAc/hexane=1:4) to give pure product (9.48 g, 69.3%). 1H NMR (400 MHz, CDCl3) δ ppm 10.35 (s, 1H), 6.86-7.03 (m, 2H), 5.53 (t, J=2.93 Hz, 1H), 3.79 (m, 1 H), 3.55-3.71 (m, 1H), 2.65 (s, 3H), 1.84-2.05 (m, 3 H), 1.51-1.78 (m, 3 H). MS (ESI) m/z=369 [M+H]+.

Provenance & Evidence