Chlorotrimethylsilane → 3-Benzylsulfanyl-4-hydroxy-6-[3-(trifluoromethoxy)phenyl]pyran-2-one

Participants

Reaction Steps

The title compound was prepared by Method A using 3'trifluoromethoxyacetophenone (3 g, 14.7 mmol), lithium bis(trimethylsilylamide (2.45 g, 14.7 mmol), chlorotrimethylsilane (2.47 g, 14.7 mmol) and diethyl ester of [(phenylmethyl)thio]propanedioic acid (1.00 g, 3.54 mmol). m.p. 128°-132° C.; 1H NMR (400 MHz, DMSO-d6) δ 4.03 (s, 2 H), 6.81 (s, 1 H), 7.2 (m, 2 H), 7.28 (m, 3 H), 7.56 (dd, 1 H), 7.69 (t, 1 H), 7.75 (s, 1 H), 7.86 (d, 1 H); IR (KBr) 2963, 1651, 1550, 1394, 1369, 1395, 1263, 1098, 1024, 800 cm-1 ; MS (CI): m/e 395 (M+H, 37), 309 (8), 273 (7), 205 (3), 119 (10); Analysis calc'd for C19H13O4S1 F3.H2O: C, 55.34; H, 3.67; found: C, 54.94; H, 4.03.

Provenance & Evidence