I am trying an reaction that convert enol to enol triflate, but I am not sure whether the crude NMR shows reaction is working.
Reaction conditions:
In an ice bath, mixture of S.M(1 eq) and DMAP (0.1eq) dissolve in dry chloroform and dry pyridine (2.1 eq). After stirring few minutes, triflic anhydride (2.1 eq) is added dropwise into the reaction mixture and stir it for overnight.
I would like some advice from experts, thanks! (:
Hi Alan,
It might be difficult to tell from the crude NMR you supplied whether there's any reactivity or the desired product is formed.
I will ask some questions I think might be able to point you in the right direction.
Q1. Have you confirmed if starting material is consumed in the reaction? I know this might sound basic but it's probably the first thing you want to verify (this can quickly be verified by TLC).
Q2. Do you've access to an LCMS? If you do, I'll suggest you start by running the LCMS of both your starting material and crude reaction mixture. This might be an alternative (faster) way to tell if you're having some product formation, if all you've is just starting material or if some other undesired reaction is occuring.
Q3. Have you taken a 19F NMR? I will also suggest you do this if you haven't already done that.
These are some of the questions I can think of for now. I'll update if more come to mind.
I also hope some follow-up answers will have better suggestions for you.
Good luck and have a nice day!
Thanks for the suggestion! Moshood Ganiu
1. The starting material is finished as shown on the TLC plate. (MeOH:EA = 1:4)
2. I have no access on LCMS as our lab mostly did purification on column chromatography only.
3. I am going to take my crude product on 13C (we only have 1H and 13C) and check whether the CF3 splitting is observed.
Alan Lee TLC looks very clean, I'm jealous lol!
Your plan sounds awesome and I hope it checks out.
Have a nice day!
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