I want to do a reaction between 1-morpholinocyclohexene and acetyl chloride to form an iminuim salt which I'll then hydrolyse to get the 2-acetylcyclohexanone. I was doing some reading about monitoring the reaction with TLC but a lot of papers say that I shouldn't monitor this reaction with TLC. I don't understand why you wouldn't want to do it for this reaction?
I wanted to use a silica-based TLC plate and in the reaction mixture will be the enamine, acetyl chloride and triethylamine which I will leave to reflux. The only thing I can think of is that maybe the acidic nature of the silica could interact with the enamine and hydrolyse it? Also the acetyl chloride can react with moisture in the air? Are there any other reasons why papers don't generally monitor c-acylation of an enamine with TLC?