I have been trying to perform what seems like a simple alkylation.
The reaction never proceeds cleanly, and although it's a simple column, yields are never above 35%.
I've tried all kinds of conditions to achieve higher yields and a cleaner reaction.
I decided to go for the big guns, and crack out the NaH for a Williamson style etherification.
Here's the bit I didn't think through. My starting material contains an azide, and although I tried to check the stability of azides to hydride, I didn't think about the by-product - hydrogen!
I couldn't find much evidence around azides and hydride, other than one or two procedures, so I figured if others had used hydride in the presence of azides it would be fine.
So I went and dissolved my material in DMF, and added the NaH, and then I froze, eyes wide, as the effervescence took hold.
There were plenty of bubbles of hydrogen, and I was, at first, a little worried.
Once hydrogen evolution had ceased, I did a quick mass spec. No evidence of azide reduction whatsoever. All I saw was the alkoxide (or sodiated starting material!). Either way no evidence of an amine, sodiated or otherwise.
It was only one equivalent of hydrogen, in a solvent that I assume doesn't dissolve it that well, without any catalyst, I don't know what I was really worried about.
Still wasn't that clean though...