Didodecyl 2-(thiophen-3-yl)malonate → Tetradodecyl benzo[1,2-b:4,5-b']dithiophene-4,4,8,8-tetracarboxylate
Reaktionsgleichung
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]([C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:23])[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:8])=[CH:2]1>CO>[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:23])([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:8])[C:2]3[S:1][CH:5]=[CH:4][C:3]=3[C:6]([C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:23])([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:8])[C:2]1=2Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
In a two-necked flask under argon, a solution of Fe(ClO4)3 in methanol (320 mL) was prepared at 0° C. A dispersion of didodecyl 2-(thiophen-3-yl)malonate in methanol (120 mL) was added to the solution. After the resulting solution was stirred at 60° C. for 4 hours under argon, the solvent was evaporated under vacuum at room temperature. After water (100 mL) was added to the residue, the aqueous layer was extracted with CH2Cl2 (100 mL×2) and the organic layer was dried and concentrated. The crude product was purified by flash chromatography (eluent: CH2Cl2:hexane=3:2) to give tetradodecyl benzo[1,2-b:4,5-b′]dithiophene-4,4,8,8-tetracarboxylate (yield: 9.0 g, 50.2%). 1H NMR (CDCl3); 0.9 (12H, t), 1.3 (72H, m), 1.7 (8H, m), 4.2 (8H, t), 7.3 (2H, d), 7.4 (2H, d).