反应详情

温度

130 °C

1-Pyreneacetic acid (1 g, 3.85 mmol), diethylene glycol (10 ml, 91.0 mmol) and p-toluenesulfonic acid (100 mg, 0.58 mmol) were mixed and heated to 130° C. for 16 h with stirring under N2. After the reaction was completed (confirmed by TLC), the reaction mixture was cooled to 20° C. and poured into 50 ml ice-water drop-wise. The aqueous reaction mixture was extracted with EtOAc (3×100 ml) and the combined organic solutions were washed with 5% aqueous KOH (2×50 ml), H2O (2×50 ml) and brine (1×50 ml), and were subsequently dried over anhydrous MgSO4. The crude product was purified by column chromatography (silica gel, EtOAc/hexanes: 1/1) to yield 1.12 g (83.59%) 15 as a light green oil. Purity: 99+% (HPLC). TLC: Rf=0.17 (EtOAc/hexanes: 1/1). 1H NMR (250 MHz, CDCl3, 20° C.): δ 8.26-7.94 (m, 9H), 4.38 (s, 2H), 4.27 (m, 2H), 3.63 (m, 2H), 3.53 (m, 2H), 3.39 (m, 2H), 2.82 (s broad, 1H). 13C NMR (125 MHz, CDCl3, 20° C.): δ 171.5, 131.3, 130.8, 130.7, 129.4, 128.3, 127.9, 127.4, 127.3, 126.0, 125.3, 125.1, 125.0, 124.8, 124.7, 123.2, 72.2, 68.9, 64.1, 61.6, 39.4.

1. temperaturethe reaction mixture was cooled to 20° C.
2. extractionThe aqueous reaction mixture was extracted with EtOAc (3×100 ml)
3. washthe combined organic solutions were washed with 5% aqueous KOH (2×50 ml), H2O (2×50 ml) and brine (1×50 ml)
4. dry with materialwere subsequently dried over anhydrous MgSO4
5. customThe crude product was purified by column chromatography (silica gel, EtOAc/hexanes: 1/1)