3-Thiocresol → 5,6-Dihydro-4-hydroxy-3-(3-methylphenylthio)-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

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Reaction Steps

The title compound was prepared as described in General Method 6 from 2.0 mmol of 3-bromo-5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one (prepared in example BBB), 2.2 mmol of 3-methylbenzenethiol, and 2.2 mmol of piperidine in 30 mL of dichloromethane. 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. 68°-70° C.). 1H NMR (DMSO-d6) δ 2.06 (s, 3 H), 2.18-2.36 (m, 3 H), 2.60 (m, 1 H), 3.38 (2 H+H2O), 6.26 (d, 1 H), 6.46 (s, 1 H), 6.75 (m, 1 H), 6.83 (t, 1 H), 7.15 (m, 3 H), 7.24 (m, 2 H), 7.45 (m, 5 H).

Provenance & Evidence