Potassium Carbonate → 5-[2-tert-butyl-4-(hydroxymethyl)-5-methyl-phenyl]sulfanyl-2-cyclopentyl-4-hydroxy-2-[2-(3-hydroxyphenyl)ethyl]-3H-pyran-6-one

Participants

Reaction Steps

The title compound was prepared as described in General Method 9 using 6-cyclopentyl-4-hydroxy-6-[2-(3-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (0.26 g, 0.9 mmol) from Example AAAAA, toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl) ester (prepared in Example FFF; 0.35 g, 1.0 mmol), 0.54 g (3.9 mmol) of K2CO3 in DMF (10 mL). The product was purified by column chromatography on silica gel eluting with EtOAc:hexane:CH2Cl2 (1:1:1) to afford the product in 81% yield as a white solid (m.p. 172°-174° C.). 1H-NMR (DMSO-d6) δ 1.47 (s, 9 H), 1.4-1.7 (m, 8 H, 1.9 (s, 3 H), 1.95-2.1 (m, 2 H), 2.35 (t, 1 H), 2.5-2.6 (m, 2 H, partially obscured by DMSO), 2.7 (q, 2 H), 4.35 (s, 2 H), 4.95 (bs, 1 H), 6.55 (t, 3 H), 6.65 (s, 1 H), 7.05 (t, 1 H), 7.25 (s, 1 H), 9.25 (s, 1 H).

Provenance & Evidence