TBDMS Chloride (Hiding the alcohol) : Molecule of the Day

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TBDMS Chloride (Hiding the alcohol)

Category: Synthesis
Posted on: October 6, 2008 9:17 PM, by Molecule of the Day

Just like boc protects amines, TBDMS protects alcohols.

TBDMS chloride will protect alcohols. The silicon-oxygen bond is pretty strong, and the silicon-fluorine bond is even better. This provides a protecting group that's pretty robust - fluoride reagents are typically used for removing the silyl ether. More on that shortly...

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Comments

It can also protect acetylenes, or at least make them more soluble and amenable to a little crystal engineering magic. Although...the awkward shape can also be sort of a hindrance there...you get a bit of disorder. :(

Posted by: psi*psi | October 6, 2008 10:59 PM

The magic fluoride reagent is [tetra-n-butyl] ammonium hydrogen bifluoride, (HF2)-. Whether you are dissolving stone or cleaving Si-O, it goes where mere F- lacks cooperation. Aqueous surface tensions can be high (dissolving stone). A drop of Dawn dishwashing liquid or a Fluorad surfactant helps.

Posted by: Uncle Al | October 7, 2008 12:07 PM

Oh my god! I just did a TBDMS protection of a primary alcohol using this very reagent (like 4 minutes ago). So weird...

Posted by: Vince Noir | October 7, 2008 9:48 PM

Also, it isn't that stable. Some 90% TFA or formic acid, or even 1% HCl in dry methanol will pop it right off. Convenient when you want to remove it with another acid-labile group, a pain in the butt for orthogonality!

Posted by: Vince Noir | October 7, 2008 9:51 PM

Xuse me, but some of your post are too condensed for a non chemist to be of interest. Perhaps the compounds are really too arcane for use outside the lab...

Posted by: Bob | October 15, 2008 1:02 AM