Chlorotrimethylsilane → HCID 13955049, compound

Participants

Reaction Conditions

Reaction Steps

Chlorotrimethylsilane (4.1 ml, 32.2 mmol) was added to lithium aluminum hydride (1.22 grams, 32.2 mmol) in THF (20 ml) at -72° C. The mixture was removed from the cold bath, stirred 2 hours, and then cooled again at -35° C. A suspension of the above 2,2'-bis(dibenzylphosphinomethyl)-1,1'-biphenyl dioxide (3.40 grams, 5.32 mmol) in THF (45 ml) was added by cannula. The mixture was stirred 0.5 hour at -30° C., then overnight at room temperature. The reaction mixture was cooled in an ice bath and quenched by the successive, dropwise addition of water (1.2 ml), 15% aqueous NaOH (1.2 ml) and water (3.6 ml). The resulting mixture was filtered, and the solid was washed with diethyl ether. The filtrate was evaporated on the steam bath under a stream of nitrogen. The residual solid was heated in ethanol, then cooled and filtered to give 2.00 grams (62% yield) of white solid, melting point 163° to 167° C. 1H NMR (CDCl3): δ 2.43 (s, 12H, benzylic); 6.50-7.17 (complex, 28H, aromatic). 31P NMR (CDCl3): δ+9.5.

Provenance & Evidence