[zhghlw]

I have been tried to use Phenylboronic acid to protect deoxynivalenol but never got the desired product. There are lots of literature reporting exactly same reaction and I just could not repeat it. The standard procedure is just mixing the deoxynivalenol and phenalboronic acid in acetone and refluxing for 10 hours. After the reaction is complete, solvent is removed to afford the product. NMR is used  to monitor the reaction since the SM and product were in the same position on TLC plate.

The SM is very expensive and I can just run the reaction in mg scale. I just mixed the SM and phenylboronic acid in a 5 ml vial and heated to the boiling point of acetone. The weird thing is  I have never got the desired product.

Anybody knows the reason why I failed the reaction? It would be greatly appreciated if you could give me some hints.

[Dan]

What do you recover after the reaction? Unchanged starting material or something else?

[zhghlw]

What do you recover after the reaction? Unchanged starting material or something else?

Thank you for your response. Just unchanged starting material. >

[Dan]

What do you recover after the reaction? Unchanged starting material or something else?

Thank you for your response. Just unchanged starting material. >

Have you NMRed your reagents to make sure they're OK? Are you using a dry solvent? I'm not sure if properly anhydrous is necessary, but acetone can be very wet.