List of used abbreviations - RosDok - Universität Rostock

General experimental procedure: To neat 3a,d-m,p (1.5 mmol) was added 13
(2.25 mmol) at –78 °C. The solution was allowed to warm to 20 °C during 20 h with
stirring. To the solution was added ammonium chloride (10%, 25 mL) and
dichloromethane. The organic and the aqueous layer were separated and the latter
was extracted with dichloromethane (3 x 20 mL). The combined organic layers were
dried (Na2SO4), filtered, and the filtrate was concentrated in vacuo and the residue
was purified by chromatography (silica gel, EtOAc / heptanes = 1:9).
S
OH
CO 2Me
CO 2Me
3-Hydroxy-5-phenylsulfanyl-phthalic acid dimethyl
ester (14a): Starting with 3a (420 mg, 1.5 mmol) and
13 (319 mg, 2.25 mmol), 14a was isolated as a highly
viscous oil (367 mg, 77%); 1 H NMR (250 MHz, CDCl3):
δ = 3.65 (s, 3 H, OCH3), 3.69 (s, 3 H, OCH3), 6.48-7.32 (m, 7H, ArH), 10.57 (s, 1H,
OH); 13 C NMR (63 MHz, CDCl3): δ = 52.6 (OCH3), 52.8 (OCH3), 106.6 (C), 116.2,
117.1, 129.5 (ArCH), 129.9 (2ArCH), 130.0 (C), 134.8 (2ArCH), 135.7, 148.3, 161.7,
168.9, 169.0 (C); IR (KBr, cm −1 ): v� = 3057 (w), 3000 (w), 2950 (w), 2845 (w), 1732
(s), 1668 (s), 1596 (s), 1556 (m), 1474 (m), 1437 (s), 1329 (s), 1265 (s), 1197 (s),
1167 (s), 1120 (s), 1068 (m), 1016 (s), 933 (m), 852 (m), 802 (m), 774 (m), 744 (s),
689 (s), 562 (m); MS (EI, 70 eV): m/z (%) = 319 (18), 318 (M + , 100), 287 (34), 285
(55), 270 (11), 269 (65), 253 (16), 228 (20), 226 (10), 200 (27), 198 (11), 171 (25);
HRMS (EI): calcd for C16H14O5S [M + ]: 318.05565, found: 318.055736.
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