ChemicalBook CAS DataBase List TRI-N-OCTYLPHOSPHINE

TRI-N-OCTYLPHOSPHINE synthesis

4synthesis methods

Product Name:TRI-N-OCTYLPHOSPHINE
CAS Number:4731-53-7
Molecular formula:C24H51P
Molecular Weight:370.64

78-50-2 Synthesis

78-50-2
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$18.00/5g

4731-53-7
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$11.19/5ML

Yield:-

Reaction Conditions:

with indium(III) bromide;1,1,3,3-Tetramethyldisiloxane in toluene at 100; for 18 h;Inert atmosphere;Sealed tube;

Steps:

4.2. General procedure for the preparation of compounds 2b to 2f and 2i to 2l
General procedure: In a sealed tube containing a solution of the phosphine oxide derivative (5 mmol) in anhydrous toluene (1 M) was added InBr₃ (1 mol %, 0.05 mmol) and the TMDS (1.5 equiv, 7.5 mmol) under an argon atmosphere. The reaction mixture was stirred at 100 °C during 7-40 h depending on the substrate (the reaction was monitored by ³¹P NMR). After complete consumption of the reagent the mixture was kept under argon in the sealed tube and cooled to 0 °C. A solution of BH₃.SMe₂ (2 M in THF, 1 equiv) was then slowly added. After 1 h at room temperature, ³¹P NMR analysis of an aliquot indicates complete conversion to phosphine borane adduct. The crude was poured in an erlenmeyer flask and silica gel was carefully added while stirring. When silica gel was added in the reaction mixture, a slightly exothermic reaction was observed. The reaction mixture was then filtered on silica gel and washed several times with ethyl acetate. After evaporation of the ethyl acetate, the residue was purified by flash chromatography on silica gel with pure cyclohexane to afford the desired phosphine-borane.

References:

Pehlivan, Leyla;Métay, Estelle;Delbrayelle, Dominique;Mignani, Gérard;Lemaire, Marc [Tetrahedron,2012,vol. 68,# 15,p. 3151 - 3155] Location in patent:supporting information; experimental part

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