Thiophenol → 4-hydroxy-2-phenethyl-2-phenyl-5-phenylsulfanyl-3H-pyran-6-one

Participants

Reaction Steps

The title compound was prepared as described in General Method 6 from 1.50 mmol of 3-bromo-5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one (prepared in example BBB), 1.60 mmol of benzenethiol, and 1.60 mmol of piperidine in 30 mL of dichloromethane. The product was triturated with hexane:ether (1:1) to afford a solid. The crude product was chromatographed on silica gel, eluting first with chloroform and then with 5% methanol in chloroform, to give the title compound (m.p. 58°-60° C.). 1H NMR (DMSO-d6)δ2.22-2.39 (m, 3H), 2.62 (m, 1H), 3.46 (q, 2H), 6.48 (m, 2H), 6.98 (m, 3H), 7.15 (m, 3H), 7.25 (m, 2H), 7.46 (m, 5H).

Provenance & Evidence