List of used abbreviations - RosDok - Universität Rostock

S
OH
3-Hydroxy-5-(2-naphthyl)sulfanyl-phthalic acid
dimethyl ester (14l): Starting with 3p (496 mg,
1.5 mmol) and 13 (319 mg, 2.25 mmol), 14l was
isolated as a highly viscous oil (298 mg, 54%); 1 H
NMR (250 MHz, CDCl3): δ = 3.68 (s, 3 H, OCH3), 3.72 (s, 3 H, OCH3), 6.56-7.92 (m,
8H, ArH), 10.60 (s, 1H, OH); 13 C NMR (63 MHz, CDCl3): δ = 52.6 (OCH3), 52.8
(OCH3), 106.6 (C), 116.4, 117.2 (ArCH), 127.2 (C), 127.3, 127.8, 127.9, 129.7, 130.9
(ArCH), 133.3, 133.8 (C), 134.7, 134.9 (ArCH), 135.8, 148.1, 161.5, 168.9, 169.0 (C);
IR (neat): ν̃ = 3052 (w), 2999 (w), 2949 (w), 2840 (w), 1731 (s), 1666 (s), 1595 (s),
1555 (s), 1497 (m), 1434 (s), 1400 (m), 1330 (s), 1264 (s), 1196 (s), 1167 (s), 1119
(s), 1016 (s), 934 (s), 850 (s), 802 (s), 742 (s), 646 (m); MS (EI, 70 eV): m/z (%) =
369 (19), 368 (M + , 100), 337 (11), 335 (17), 319 (24), 303 (18), 250 (19), 248 (10),
221 (12); HRMS (EI): calcd for C20H16O5S [M + ]: 368.07130, found: 368.071809.
General procedure for the synthesis of 17a-c: To a dichloromethane solution (10
mL / mmol of 15) of 15 (1.65 mmol) and of 16 (1.5 mmol) was added TiCl4 (1.5 mmol)
at –78 °C. The solution was allowed to warm to 20 °C within 20 h. To the solution
was added a saturated aqueous solution of 10% HCl (15 mL). The organic and the
aqueous layer were separated and the latter was extracted with CH2Cl2 (3 x 20 mL).
The combined organic layers were dried (Na2SO4), filtered, and the filtrate was
concentrated in vacuo. The residue was purified by chromatography (silica gel,
EtOAc / n-heptane = 1:4).
CO 2Me
CO 2Me
88