Toluene → 1-(4-Methoxyphenyl)-2-(2-cyanothiophen-5-yl)acetylene

Participants

Reaction Steps

A mixture of sodium ethoxide (0.7 g), 1-(4-methoxyphenyl)acetylene (0.5 g), and toluene (40 cm3) is stirred for 2 h, 2-bromo-5-cyanothiophene (0.7 g), is added and the resultant mixture heated under reflux for 3 h. The reaction mixture is poured into water (500 cm3) and the organic layer separated off. The aqueous layer is then extracted with toluene (2×50 cm3). The combined organic layers are washed with water (2×200 cm3), dried (MgSO4), filtered and then evaporated down. The residue is purified by column chromatography on silica gel using a 95:5 hexane/ethyl acetate mixture as eluent and recrystallisation from ethanol to yield 0.3 g of 1-(4-methoxyphenyl)-2-(2-cyanothiophen-5-yl)acetylene.

Provenance & Evidence