I have protected cyanoacetic acid with TBDMSiCl (with imidazole as base). I stopped the reaction, washed with water and then with pentane but I can't obtain the product pure (there are even the two reactants). Anyone knows how remove cyanoacetic acid and TBDMSiCl from the medium? The product is an oil
Thanks
You can follow the following steps:
1- Treat the produse with sodium bicarbonate solution.
2- use a separation funnel with the presence of ether to separate the organic product.
3- Removal of water layer that containing imidazole and carboxylic acid salt when interacting with bicarbonate solution.
4- Keep the ether layer. Then, evaporate the ether to get the corresponding pure product.
The compound contains two functional groups, a nitrile (−C≡N) and a carboxylic acid You can remove cyanoacetic acid by neutralization with aque. NaOH(10%) and TBDMSiCl on treatment with 1M aque.NaOH by hydrolysis.
You can follow the following steps:
1- Treat the produse with sodium bicarbonate solution.
2- use a separation funnel with the presence of ether to separate the organic product.
3- Removal of water layer that containing imidazole and carboxylic acid salt when interacting with bicarbonate solution.
4- Keep the ether layer. Then, evaporate the ether to get the corresponding pure product.
You may get the reaction to go to completion by adding some dimethylaminopyridine - see Carb. Res., 1991, 218, 95-109. (Referenced by Tet. Lett, 2009, 3702-3705.) Do you knowthat your product is soluble in pentane? Also, if the cyanoacetate and imidazole are coming from hydrolysis, a few drops of acetic acid just prior to workup might help.
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