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Author: Subject: Workup of NaBH4,I2, THF rxn?
maniacscientist
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[*] posted on 7-10-2007 at 08:12
Workup of NaBH4,I2, THF rxn?


Hi to all out there,

I´ve stumbled across this paper (great forum btw) and I already did this reaction a long time ago for reducing aminoacids to alcohols.

I have a few questions since I don´t possess the relevant papers anymore.

1.Does the addition of the catalyst to the Iodine or vice versa need reflux to form the desired BH3-THF complex or is the cooled addition sufficient?

2. I remeber lot of salt percipitated but didn´t cause much of a problem since it was washed with ether to regain any remnant product of it.

3. Concluding to this paper: www.sciencemadness.org/talk/viewthread.php?action=attachment...

they clean up the product by cromatography or by addition of trifluorBoretherate and then base-extraction.

Is this last step a must or would it be sufficient to just separate and basify and extract.

We´ve learned NaBH4 rxns are quenchend and then some Me(OH) is added and evaporated to eliminate any borane residue, should this be done? I think I did it, when I was performing this reaction, I recovered the product in very good yield, but I don´t remeber,... -could well be that I scipped the Me(OH)-step.

if you on this great board could shed some light onto this, I´d be really thankful!

Maniacscientist

[Edited on 7-10-2007 by maniacscientist]
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maniacscientist
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[*] posted on 7-10-2007 at 08:55


found it myself
-> 0°C addition is sufficient with 15min. stirring to from the desired borane-ether complex.
-> workup is easy and just need separating and a/b extraction to recover the product

thanks a lot!
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