Reaktion #319621

Reaktionsgleichung

2,2'-bis(dibenzylphosphinomethyl)-1,1'-biphenyl dioxide

Chlorotrimethylsilane

lithium aluminum hydride

→

white solid

Ausbeute 62.0%

2,2'-Bis(dibenzylphosphinomethyl)-1,1'-biphenyl

Ausbeute 62.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was removed from the cold bath
2. 2
   workup.ADDITIONwas added by cannula
3. 3
   workup.STIRRINGThe mixture was stirred 0.5 hour at -30° C.
4. 4
   Sonstigeovernight
5. 5
   Sonstigeat room temperature
6. 6
   TemperaturThe reaction mixture was cooled in an ice bath
7. 7
   Sonstigequenched by the successive,
8. 8
   workup.ADDITIONdropwise addition of water (1.2 ml), 15% aqueous NaOH (1.2 ml) and water (3.6 ml)
9. 9
   FiltrationThe resulting mixture was filtered
10. 10
    Waschenthe solid was washed with diethyl ether
11. 11
    SonstigeThe filtrate was evaporated on the steam bath under a stream of nitrogen
12. 12
    TemperaturThe residual solid was heated in ethanol
13. 13
    Temperaturcooled
14. 14
    Filtrationfiltered

Vorschrift

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.

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