Water → Trifluoro-methanesulfonic acid 5-(3-benzyloxy-phenoxy)-2-formyl-3-methyl-phenyl ester

Participants

Reaction Steps

To a solution of 4-(3-benzyloxy-phenoxy)-2-hydroxy-6-methyl-benzaldehyde (2.5 g, 6.5 mmol) and Et3N (2.72 mL, 19.5 mmol) in DCM (60 mL) at −78° C. was added Tf2O (1.64 mL, 9.76 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 3 hours. Water was added and the solution extracted with DCM (2×25 mL). The organic extracts were dried and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (hexane:EtOAc 80:20) to give trifluoro-methanesulfonic acid 5-(3-benzyloxy-phenoxy)-2-formyl-3-methyl-phenyl ester (2.8 g, 93%). 1H NMR (400 MHz, CDCl3): δ 10.36 (s, 1H), 7.43-7.32 (m, 6H), 6.90 (dd, J=2.0, 8.4 Hz, 1H), 6.79-6.67 (m, 4H), 5.06 (s, 2H), 2.61 (s, 3H). MS (ESI) m/z=467 [M+H]+.

Provenance & Evidence