Triethylamine → Trifluoro-methanesulfonic acid 2-formyl-3-methoxymethyl-5-(tetrahydro-pyran-2-yloxy)-phenyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-hydroxy-6-methoxymethyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (3.09 g, 11.62 mmol) and Et3N (6.47 mL, 46.48 mmol) in dichloromethane (50 mL) was added Tf2O (4.30 mL, 25.56 mmol) at −78° C. The mixture was stirred at −78° C. for 1 hour. The mixture was diluted with H2O and extracted with dichloromethane. The organic extracts were washed with brine, dried and concentrated in vacuo. The residue was dissolved in Hexane-EtOAc(4:1), filtered through a plug of silica gel and filtrate was concentrated to give trifluoro-methanesulfonic acid 2-formyl-3-methoxymethyl-5-(tetrahydro-pyran-2-yloxy)-phenyl ester (2.60 g, 72%). 1H NMR (400 MHz, CDCl3) δ 10.30 (s, 1H), 7.44 (s, 1H), 7.00 (s, 1H), 5.60 (s, 1H), 4.80 (s, 2H), 3.80 (m, 1H), 3.65 (m, 1H), 3.50 (s, 3H), 2.00-1.50 (m, 6H).

Provenance & Evidence