Reduction of azide by triphenyl phosphine ( TPP) :
Reaction time is about 10 Hrs, Its quite difficult for work up, major problem is removal of excess TPP. There are serval methods in that,
1) If you will face the problem with TPP in the future you can try to add CuCl to the solution of your crude product in acetone. CuClxTPP complex is insoluble in this solvent....
2) If your impurity is TPPO, its solubility in diethyl ether is not good, and you will need large amount of ether if you want to extract all TPPO; in this case most likely you will loose a lot of your product as well.
From my experience, in most cases TPPO happens to be more polar than the product and washing the crude mixture with non-polar solvent (like hexane or hexane-ether mixture) allows to extract the product from insoluble TPPO.
3) Check the solubility of your product and non soluble nature of triphenylphosphine with different solvent.Or use column chromatography with change of polarity of solvent
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