Tetrahydrofuran → HCID 12058650, compound

Participants

Reaction Steps

To a suspension of lithium (2.1 g, 0.3 g atom) in 150 ml of anhydrous tetrahydrofuran held under nitrogen, a solution of triphenylphosphine (26.2 g, 0.1 ml) in 150 ml dry tetrahydrofuran is added in a period of 1/2 hour. The temperature rises from 25° C to 55° C. The solution turns blood-red and nearly all of the lithium dissolves in 3 hours. To this solution t-butyl chloride (9.3 g, 0.1 mol) is added to destroy the phenyl lithium. The solution is filtered, and to it 4-chlorophenyl triethoxysilane (27.5 g, 0.1 mol) dissolved in 50 ml of dry tetrahydrofuran is added and the solution refluxed 4 hours. The red color is not fully discharged in this time due to the sluggish nature of the nucleophilic displacement of the aryl chloride. The excess lithium diphenylphosphide is destroyed by addition of 25 ml of ethanol and finally, water. The solvents are removed in vacuum. The liquid is taken up in toluene and filtered to remove precipitated lithium chloride. Gas-liquid chromatographic analysis of this solution shows the presence of recovered chlorophenyl silane, triphenylphosphine, and only a small amount (estimated 15 percent yield) of 4-(diphenylphosphinyl)phenyl triethoxysilane.

Provenance & Evidence