Triethylamine → 4-[2-Methyl-4-(tetrahydro-pyran-2-yloxy)-6-trifluoromethanesulfonyloxy-phenyl]-4-oxo-butyric acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[2-hydroxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-4-oxo-butyric acid methyl ester (2.87 g, 8.91 mmol) and Et3N (3.71 mL, 26.73 mmol) in dichloromethane (30 mL) was added Tf2O (2.30 mL, 13.37 mmol) at −78° C. The mixture was stirred at −78° C. for 2 hours, 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 4-[2-methyl-4-(tetrahydro-pyran-2-yloxy)-6-trifluoromethanesulfonyloxy-phenyl]-4-oxo-butyric acid methyl ester (2.56 g, 63%). 1HNMR (400 MHz, CDCl3): 6.95 (s, 1H), 6.90 (s, 1H), 5.45 (s, 1H), 3.82 (m, 1H), 3.77 (s, 3H), 3.65 (m, 1H), 3.10 (t, J=6.5 Hz, 2H), 2.75 (t, J=6.5 Hz, 2H), 2.30 (s, 3H), 2.05-1.50 (m, 6H).

Provenance & Evidence