Triethylamine → 3-(Biphenyl-2-ylmethylthio)-5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared as described in General Method 7 using the following: 5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one (0.250 g, 0.94 mmol), (2-methylbiphenyl)-p-toluenethiosulfonate (0.389 g, 1.1 mmol), Et3N (0.26 mL, 1.9 mmol), absolute ethanol (5.0 mL), NaHCO3 (0.5 g). The mixture was heated to 40° C. for 16 h, then diluted with diethyl ether (100 mL) and washed with H2O. The solvent was then removed in vacuo and the residue submitted to column chromatography (SiO2, 100% CH2Cl2 to 2% methanol in CH2Cl2) to provide a thick oil (0.286 g). 1H NMR (400 MHz, DMSO-d6) δ11.770 (bs, 1H), 7.434-7.148 (m, 18H), 6.969 (d, 1H, J=7 Hz), 3.595 (s, 2H), 3.407 (s, 2H).

Provenance & Evidence