I tried to synthesize 2-(6-fluoropyridin-3-yl) acetic acid from 5-(Chloromethyl)-2-fluoropyridine using Pd(OAc)2/PPh3 catalyst,Na2CO3 and DCC. I eluted my product on TLC with Ethyl acetate/hexane/acetic acid with a 1:4:1 ratio and I saw a spot for my compound. I extracted my compound with water and chloroform to remove any salts and then did silica chromatography to remove Pd. But when I took the NMR of the compound I could not see any peaks in the aromatic range for the pyridine ring, and it seems my compound has decomposed. I cannot figure out where is the problem. Does anyone have any clue to help with this issue?
5
-
1$\begingroup$ Did you recheck by TLC after the CHCl3/water extraction including checking the aq phase? $\endgroup$– WaylanderCommented Apr 15 at 5:44
-
1$\begingroup$ Yes, I did. The spot was the same for the organic phase and no spot for the aqueous phase $\endgroup$– EllaCommented Apr 19 at 5:28
-
$\begingroup$ If you have a reference compound, you could try to make a "co-spot", meaning that you put a droplet of your product and the ref. compound at the same spot as well as their individual spots and watch whether the signal belongs to the same compound. $\endgroup$– int 21h Glory to UkraineCommented Apr 19 at 6:25
-
$\begingroup$ Did you see the compound spot by TLC in the column fractions? $\endgroup$– WaylanderCommented Apr 19 at 6:43
-
$\begingroup$ Have you considered taking your starting material and reacting it with KCN in DMF then hydrolysing? $\endgroup$– WaylanderCommented Apr 19 at 18:09
Add a comment
|