Chlorotrimethylsilane → [4,5-Bis(4-methoxyphenyl)thiophen-2-yl](trimethyl)silane

Participants

Reaction Steps

2,3-Bis(4-methoxyphenyl)thiophene (5.92 g, 20 mmole) was dissolved in 100 ml toluene and the volume reduced by approximately 3/4 by distillation. The cooled solution was diluted with 130 ml diethyl ether, cooled to ~10° and treated with 1.55 M n-butyl lithium (15.5 ml, 1.2 equiv.). The reaction mixture was heated at reflux for 1.5 hours, cooled to 0° and treated dropwise with a solution of trimethylsilyl chloride (3.1 ml, 1.2 equiv.) in 5 ml diethyl ether. The reaction mixture was stirred overnight at room temperature and then quenched with water.

Provenance & Evidence