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

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Reaction Steps

The title compound was prepared by Method A using 4'-(3-phenylpropoxy)acetophenone (1.28 g, 5.06 mmol), lithium bis(trimethylsilyl)amide (0.930 g, 5.56 mmol), chlorotrimethylsilane (0.705 mL, 5.56 mmol), THF (57 mL), and diethyl ester of [(2-phenylethyl)thio]propanedioic acid (1.00 g, 3.37 mmol). m.p. 139-142° C.; 1H NMR (400 MHz, DMSO-d6) δ2.04 (m, 2 H), 2.84 (m, 4 H), 2.98 (t, 2 H), 4.40 (t, 2 H), 6.68 (s, 1 H), 7.18 (m, 12 H), 7.75 (d, 2 H), 11.86 (bs, 1 H).

Provenance & Evidence