[AlphaScent]

So if I wanted to take a secondary alcohol to the ketone, it would not be that difficult.  But if I wanted to take a large amount of the alcohol to the ketone, things start to change.  PCC is out.

I have a method for TEMPO but the paper I reference says 2-octanol has no reaction.

I am thinking Swern because I know it and it will work.

Has anyone had success even on small scale with TEMPO?

Cheers!!

[discodermolide]

Yes, TEMPO and bleach. I think we discussed this before.
Swern you can do. If you know the reaction and know it works then use it. Be careful.

[zsinger]

Swern….But DMS is NASTY NASTY NASTY…..be careful.  This is a time where the Swern is the appropriate reaction to use.
          -Zack

[AlphaScent]

We have 100% discussed this before, disco.

The discodermolide reference is a primary alcohol.  I was just wondering if anyone has done TEMPO on a secondary alcohol.

My TEMPO reaction: 5% TEMPO; 5% potassium t-butoxide; 5% CuBr2; 5% bis-pyridine in ACN/water while pumping oxygen through the solution does not work for secondary alcohols according to the reference.

Your discodermolide reference will work for promary, secondary, allylic, benzylic and propargylic alcohols??

Want to clear th

[AlphaScent]

Just want to be clear on the use of that reaction. 

I will use it in the future.

[phth]

Reported 99% yield for 2-octanol under these conditions. Ref: http://pubs.acs.org/doi/abs/10.1021/jo00388a038

[orgopete]

Reported 99% yield for 2-octanol under these conditions. Ref: http://pubs.acs.org/doi/abs/10.1021/jo00388a038

I don't mean to jump in because I don't have a real contribution, except this is my favorite kind of answer, a literature citation. Kudos!

[AlphaScent]

Great paper.  right along the lines of discos reference.