Chlorotrimethylsilane → 4-Hydroxy-6-[2-hydroxy-3-methyl-4-(phenylmethoxy)phenyl]-3-[(2-phenylethyl)thio]-2H-pyran-2-one

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Reaction Steps

The title compound was prepared by Method A using 4'-benzyloxy-2'-hydroxy-3'-methylacetophenone (1.29 g, 5.06 mmol), lithium bis(trimethylsilyl)amide (2.11 g, 12.6 mmol), chlorotrimethylsilane (1.60 mL, 12.6 mmol), THF (127 mL), and diethyl ester of [(2-phenylethyl)thio]propanedioic acid (1.00 g, 3.37 mmol). m.p. 147-148° C.; 1H NMR (400 MHz, DMSO-d6) δ2.14 (s, 3 H), 2.77 (t, 2 H), 2.98 (t, 2 H), 5.17 (s, 2 H), 5.29 (s, 1 H), 6.79 (d, 1 H), 7.30 (m, 13H), 9.36 (s, 1 H), 11.85 (bs, 1 H).

Provenance & Evidence