Pyridine → HCID 10802961, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-hydroxy-4-methoxy-benzaldehyde (30 g, 197 mmol) in DCM (anhydrous, 120 mL) was added pyridine (79 mL, 986 mmol) at room temperature. After the mixture was cooled to −10° C., the Tf2O (50 mL, 296 mmol) was slowly added to the reaction between −10° C. to 0° C. The addition took about 2.5 hours. After the addition, the stirring was kept for 30 minutes. The EtOAc (200 mL) was added. The organic layer was washed with 1 M HCl (3×80 mL), dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified over silica gel, eluting with 5% EtOAc/hexanes to give trifluoro-methanesulfonic acid 2-formyl-5-methoxy-phenyl ester (2) 46 g in 82% yield. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.13 (s, 1 H), 7.95 (d, J=8.99 Hz, 1 H), 7.03 (dd, J=8.60, 2.34 Hz, 1 H), 6.88 (d, J=2.34 Hz, 1 H), 3.93 (s, 3 H)

Provenance & Evidence