Réaction #157504

Équation de réaction

4-hydroxy-3-(methoxy)benzaldehyde

Et3N

Tf2O

→

title compound

4-formyl-2-(methoxy)phenyl trifluoromethanesulfonate

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Lavagewashed (water, brine)
2. 2
   Séchagedried over Na2SO4
3. 3
   Concentrationconcentrated in vacuo
4. 4
   AutreThe residue was purified by flash chromatography (EtOAc/hexanes)

Mode opératoire

To a solution of 4-hydroxy-3-(methoxy)benzaldehyde (0.760 g; 5.00 mmol) and Et3N (1.39 mL; 10.0 mmol) in anhyd CH2Cl2 (10 mL) at 0° C. was added Tf2O (0.92 mL; 5.5 mmol), dropwise over 2 min. The mixture was allowed to warm slowly to room temperature (overnight), diluted with CH2Cl2, washed (water, brine), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 4.01 (s, 3H), 7.42 (d, J=8.2 Hz, 1H), 7.52 (dd, J=8.2, 1.8 Hz, 1H), 7.57 (d, J=1.7 Hz, 1H), 9.99 (s, 1H).

Source