[jake.n]

I'm writing a research proposal for my advanced organic class and I need to find an appropriate protecting group for my hydroxy group.  I am faimilar with some protecting groups (eg. silyl ethers, trityl, benzoyl) but what makes one group better than another?  If you could point me towards some references it would be appreciated.  All I can find using Scifinder is alcohol oxidation-tandem olefinations, which I do not want.

[MissPhosgene]

The answer kind of depends on what n can be. So, what is the range or number for n?

[discodermolide]

The choice of protection really depends on what you want to do later in the synthesis.

[sjb]

If all your halide for Wittig is is the bromo-alcohol as drawn, why not just add another equivalent of base when you form the ylid, then perhaps look at protection after attachment, if it's still needed?

[jake.n]

n will be in the 2-4 range.  If I can do the olefination without protecting the alcohol that would be great, too.  I just want to prevent further oxidation.

[discodermolide]

n will be in the 2-4 range.  If I can do the olefination without protecting the alcohol that would be great, too.  I just want to prevent further oxidation.

Oxidation???
Just use 2 or more equivalents of base

[MissPhosgene]

Instead of oxidation, I would be worried about the reactant snapping shut with certain values of n.

[jake.n]

I guess oxidation was not the correct wordage.  I was worried about my alkane snapping shut, as some of you mentioned.

Edit:  I found a couple of references to cite for the two eq. base method.  Thanks for the help