How to reduce an Ester to aldehyde with no alcohol formation?
However, what I see is three spots. One of my aldehyde, the other should be alcohol much more polar and the last one I'm not sure what it is. Has anyone done this reaction and got exclusively the aldehyde? During my synthesis of anhydro levuglandin D2 I had to reduce a lactone to an aldehyde. National University of Singapore. There are more reagents to do the selective oxidation then do selective reduction. One of the protocols for obtaining the reagent you find in work Kim et al. Tetrahedron Lett 48 , Reference and notes: Dear Matheus Andrade Meirelles.
You need to detect the products using NMR and see if you obtained alcohol and beside aldehyde or not and if so, how much percent alcohol you get and then you can decide if this method is suitable or not. Thank a lot guys. I checked by NMR and after 4 hours of reaction, even after adding 3eq. I may try other condition for this reaction, if those don't work, I'll try something different. Eugene, at first I was thinking of doing the 2 steps, reduction to alcohol and oxidation to aldehyde.
However, I found a paper that uses this methodology with morpholine and I got curious on that. Bruce and Adam, thank for the suggestions, I may try it. Yes, you need a new method. I think you may try Eugene suggestion to reduce down to the alcohol and selectively oxidise back to the aldehyde.
According to my experience, in this type reduction controlling the reaction condition particularly temperature is extremely important. Depending on the reactivity of your ester, the optimal temperature can vary from C to C, but it is still difficult to get the aldehyde exclusively. Diisobutylaluminium Hydride DIBALH , very widely used reducing agent especially for reducing esters esters can be reduced to either the aldehyde or the alcohol depending on the stoichiometry and reaction conditions:.
See the full ppt. Using of sodium in ethanol in reduction of ester known as Bouveault—Blanc reduction leading to the formation of alcohol. Have a look at. My method might solve your problem. Would you please, send us your nice interested paper P. I'm still looking for some methods in order to avoid those two steps and go directly from ester to aldehyde.
Could you please send us your paper Dr. You will have to find my article in a library. As you mentioned, the full text of the paper isn't found in your library. Do you've the volume and page numbers?. I use mno2 in chloroform to oxidize alcohol to aldehyde but the reaction no longer works. Could any one help me. Can you help by adding an answer? Question followers 15 See all.
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