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

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Reaction Steps

The compound was synthesized following General Method 9 and using 172 mg (0.5 mmol) of 4-hydroxy-6,6-bis-[2-(3-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example XX), 179 mg (0.5 mmol) of toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl) ester (prepared in Example FFF), 270 mg (2.0 mmol) of K2CO3, and 2 mL of DMF. The reaction was worked up as described and chromatographed on silica get eluting with (1:1 CH2Cl2 :EtOAc+2% MeOH), to yield the title compound, m.p. 92°-94° C. 1H NMR (DMSO-d6) δ 1.48 (s, 9 H), 1.80 (s, 3 H), 2,07 (m, 4 H), 2.6 (m, 4 H), 3.0 (s, 2 H), 4.35 (s, 2 H), 6.6 (m, 6 H), 6.65 (s, 1 H), 7.05 (t, 2 H), 7.25 (s, 1 H), 9.25 (s, 2 H).

Provenance & Evidence