Hydrochloric Acid → 4-(5-Hexyl-2-pyrimidinyl)phenyl 5-dodecylthiophene-2-carboxylate

Participants

Reaction Steps

15 ml of pyridine was added to 0.49 g (1.93×10-3 mol) of 4-(5-hexyl-2-pyrimidinyl)phenol, followed by cooling on an iced water bath. To the mixture, 0.61 g (1.93×10-3 mol) of 5-dodecylthiophene-2-carboxylic chloride was added, followed by stirring for 4.5 hours at room temperature. After the reaction, the reaction mixture was poured into 100 ml of water and acidified with conc. hydrochloric acid, followed by three times of extraction with 50 ml of isopropyl ether. The organic layer was washed with water repeatedly until the washing liquid reached neutrality, followed by drying with anhydrous magnesium sulfate and distilling-off of the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography with the use of a hexane/ethyl acetate (=10/1) mixture solvent and recrystallized from an ethanol/ethyl acetate mixture solvent to obtain 0.52 g of a pure product (yield: 50.5%). ##STR32##

Provenance & Evidence