[zq]

Can we deprotonate benzylic alcohols with triethyl amine or DIPEA? I don't want to use NaH for some reasons.

[Transmutation]

No.  You can deprotonate phenols with those bases, but not benzylic alcohols.  If the molecule can't handle strong base, then you are out of luck, because the alkoxide itself would be a pretty strong base.  I'm guessing pKa of the conjugate acid around 16?

If you can use a strong base, LDA may be a good choice for this.

[Shaun]

What reaction are you interested in doing?  If you are doing an acylation, tertiary amine-type bases work (TEA, pyridine etc).  In these reactions, however, the alcohol isn't deprotonated.  They simply act as a base to neutralize the acid that is generated.

If you need to actually deprotonate the alcohol then these bases do not work.

NaH can dangerous to use if you aren't accustomed to doing organic synthesis.  The mineral oil suspension form is really quite safe and can be measured out on a balance easily.  The pure powder form of NaH is much worse but it is still ok to use if you keep everything away from moisture.

For a lot of reactions you can get away with using cesium carbonate which is very easy to handle.