Potassium Carbonate → 3-(2-tert-Butyl-4-hydroxymethyl-5-methylphenylsulfanyl)-4-hydroxy-6,6-bis-[2-(4-hydroxyphenyl)ethyl]-5,6-dihydropyran-2-one

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Reaction Steps

The title compound was prepared as described in General Method 9 using 0.14 g (0.39 mmol) of 4-hydroxy-6,6-bis [2-(4-hydroxyphenyl)ethyl]-5,6-dihydro-pyran-2-one (prepared in Example PP), 0.19 g (0.52 mmol) of toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl) ester (prepared in Example FFF), 0.22 g (1.6 mmol) of K2CO3, and 3 mL of DMF. The solution was stirred overnight at room temperature. Purification by silica gel chromatography, eluting with CH2Cl2 :MeOH (100:0 to 90:10), gave the title compound, m.p. 192-194° C. 1H NMR (DMSO-d6) δ 1.48 (s, 9 H), 1.83 (s, 3 H), 2.02 (m, 4 H), 2.54 (m, 4 H), 2.96 (br s, 2 H), 4.35 (br s, 2 H), 4.94 (br a, 1 H), 6.68 (m, 5 H), 6.99 (dd, 4 H), 7.26 (s, 1 H), 9.16 (s, 2 H).

Provenance & Evidence