Dichlorodimethylsilane → [4,5-Bis(4-methoxyphenyl)thiophen-2-yl](dimethyl)silane

Participants

Reaction Steps

A solution of 2,3-bis(4-methoxyphenyl)thiophene (5.92 g, 20 mmole) in 100 ml diethyl ether/20 ml toluene was treated with 1.6 M n-butyl lithium (14 ml, 1.12 equiv.) and heated at reflux for 1.5 hours. The reaction mixture was cooled to -76° and cannulated into a solution of dimethyldichlorosilane (4.6 ml, 1.9 equiv.) in 40 ml diethyl ether at -76°. After 2.5 hours, the reaction mixture was treated with a diisobutylaluminum hydride tetramethylethylenediamine complex prepared by addition of tetramethylethylenediamine (9.9 ml, 66 mmole) to 1 M diisobutylaluminum hydride in hexane (66 ml, 66 mmole). The reaction mixture was stirred 2 hours at 0°, recooled to -30° and quenched with saturated aqueous potassium-sodium tartrate.

Provenance & Evidence