Taking the Long Way to Chicago ACS

Well I finally made it to Chicago for the American Chemical Society meeting on Saturday.

The bad news is that my 9:35 flight from Philly was canceled and I had to take another then ended up leaving at 17:00.

The good news is that I was stranded in the airport with Bruce Ganem from Cornell. As luck would have it Bruce is also working on multi-component reactions, including the Ugi reaction and his version of a 5-component Ugi involving nitrile and organometalic components. He received the ACS award for Creative Invention yesterday.

Needless to say, I was eager to get his opinion on our little puzzle of the disappearing methyl. He was reminded of the acid-catalysed hydrolysis of furans leading to the opening of the ring. This might open the door deprotonating the methyl as shown below. Lots of things could happen from this point, including cyclizations. When I have more time I'll see how we could get that pair of doublets, with one of them massively deshielded at 8.4 ppm. I am wondering if that peak stays there after neutralization. Time will tell.

More on the ACS shortly....

I hope to meet up with some of you at the conference.
There is a chemistry blogging meeting at 13:00 today and a Blue Obelisk dinner at 19:00 on Tuesday.