Water → HCID 59207325, compound

Participants

Reaction Conditions

Reaction Steps

5-(4-{5′-[4-(4-Carboxy-butyl)-phenyl]-[2,2′]bithiophenyl-5-yl}-phenyl)-pentanoic acid (1.05 g, 2.02 mmol) and 1,4-pentadien-3-ol (0.42 g, 5.0 mmol) are suspended in NMP (52 mL). 1-(3-Dimethlaminopropyl)-3-ethylcarbodiimide hydrochloride [EDCI] (0.96 g, 5.0 mmol) is added, followed by 4-dimethylaminopyridine (0.61 g, 4.9 mmol) and the mixture is warmed to 50° C. for 10 min. The resulting solution is stirred at room temperature for 3 days. The mixture is poured into water (300 ml) and the resulting precipitate filtered. The solid is dissolved in THF (300 mL), filtered and dry loaded onto silica. The silica is loaded onto a dry silica column and eluted with petrol/dichloromethane (4:1) to remove non-coloured products. The eluent is changed to chloroform and the coloured fractions are collected to afford crude product (1.06 g). A portion (0.5 g) is further purified by reverse phase chromatography (eluent: acetonitrile/THF 9:1 to 1:1, gradient). Final recrystallisation from ethyl acetate afforded the product (0.15 g). 1H NMR (300 MHz, CDCl3): δ (ppm) 7.51 (d, 4H), 7.20 (s, 4H), 7.14 (d, 4H), 5.83 (m, 4H), 5.71 (m, 2H), 5.25 (m, 8H), 2.64 (t, 4H), 2.38 (t,0 4H), 1.73-1.63 (m, 8H); 13C NMR (75 MHz, CDCl3): δ (ppm) 172.4, 143.2, 142.8, 136.4, 135.2, 129.0, 125.6, 125.5, 124.4, 123.4, 117.4, 74.9, 34.9, 34.0, 30.1, 25.9. m.p. (° C.) K 75 SX 174 I.

Provenance & Evidence