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Hallo,
i am doing a synthesis of an oxime from tert-butyl acetoacetate using NaNO2 in acetic acid. (I am sorry for that I do not know the way to upload an image to describe the reaction scheme that may help make it clearly understood, but I hope you can get the topic).
I follow the procedure described in Tetrahedron Asymmetry, 1991, 2, 555. It was reported that from tert-butyl acetoacetate, a white solid product with m.p. of 68 OC was obtained in high yield.
I have obtained an colorless oil. I suppose that it is still a mixture of the product (oxime), tert-butyl acetoacetate and probably acetic acid.
I will try to improve the operation to get the compound in high yield so that i do not have to care much about purification. However, I am thinking a way to separate the oxime from the mixture I have got today-the result of my first experiment concerning the topic. I still do not have a sound idea, how to do it. I do not think that recrystalization may help because it seems that the mixture contains considerable amounts of the starting materials. Column chromatography may help but I could not do TLC to look for a proper solvent system since the compounds may be invisible under UV light.
I appreciate any of your suggestions.
Thank you.
CPC
