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

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Reaction Conditions

Reaction Steps

To a solution of 2-ethyl-6-hydroxy-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (1.56 g, 6.24 mmol) and Et3N (2.61 mL, 18.72 mmol) in dichloromethane (20 mL) was slowly added Tf2O (2.10 mL, 12.84 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 3-ethyl-2-formyl-5-(tetrahydro-pyran-2-yloxy)-phenyl ester (2.06 g, quant.). 1H NMR (400 MHz, CDCl3δ 12.39 (s, 1H), 10.08 (s, 1H), 6.98 (s, 1H), 6.90 (s, 1H), 5.50 (s, 1H), 3.80 (m, 1H), 3.66 (m, 1H), 3.07 (m, 2H), 2.00-1.50 (m, 6H), 1.26 (m, 3H).

Provenance & Evidence