Triethylamine → 4-hydroxy-2-isopentyl-2-phenyl-5-[(2-phenylphenyl)methylsulfanyl]-3H-pyran-6-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-phenyl-6-(3-methylbutyl)-2H-pyran-2-one (0.250 g, 0.96 mmol), (2-methylbiphenyl)-p-toluenethiosulfonate (0.439 g, 1.24 mmol), Et3N (0.17 mL, 1.24 mmol), absolute ethanol (3.0 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 solid (0.33 g, m.p. 49°-51° C.). 1H NMR (400 MHz, DMSO-d6) δ7.425-7.153 (m, 13H), 7.74 (dd, 1H, J=1 Hz, J=7 Hz), 3.480 (dd, 2H, J=12 Hz, J=17 Hz), 3.149 (dd, 2H, J=17 Hz, J=22 Hz), 1.921-1.821 (m, 2H), 1.402-1.336 (m, 1H), 1.161-1.071 (m, 1H), 0.847-0.707 (m, 7H).

Provenance & Evidence