Tert-Butyldimethylsilyl_chloride

<i>tert</i>-Butyldimethylsilyl chloride

tert-Butyldimethylsilyl chloride

Chemical compound

tert-Butyldimethylsilyl chloride is an organosilicon compound with the formula (Me3C)Me2SiCl (Me = CH3). It is commonly abbreviated as TBSCl or TBDMSCl. It is a chlorosilane containing two methyl groups and a tert-butyl group. As such it is more bulky that trimethylsilyl chloride. It is a colorless or white solid that is soluble in many organic solvents but reacts with water and alcohols. The compound is used to protect alcohols in organic synthesis.[1]

Quick Facts Names, Identifiers ...

tert-Butyldimethylsilyl chloride reacts with alcohols in the presence of base to give tert-butyldimethylsilyl ethers:[2][3]

(Me3C)Me2SiCl + ROH → (Me3C)Me2SiOR + HCl

These silyl ethers hydrolyze much more slowly than the trimethylsilyl ethers.

It also can silylate terminal alkynes.[4]

The triflate derivative (Me3C)Me2SiOTf is used similarly but is more reactive.[5][6]

References

  1. [1]
    Bret E. Huff; Wenming Zhang (2008). "t-Butyldimethylchlorosilane". EROS. doi:10.1002/047084289X.rb373.pub2. ISBN 978-0-471-93623-7.
  2. [2]
    Bajwa, Joginder S.; Prasad, Kapa; Repic, Oljan (2006). "2-(2',2'-Dimethylpropoxy)-2,3-Dihydro-1H-Indene". Organic Syntheses. 83: 155. doi:10.15227/orgsyn.083.0155.
  3. [3]
    Paquette; Heidelbaugh, Todd M. (1996). "tert-Butyldimethylsiloxy-2-cyclopenten-1-one". Organic Syntheses. 73: 44first1=Leo A. doi:10.15227/orgsyn.073.0044.
  4. [4]
    Marshall, James A.; Yanik, Mathew M.; Adams, Nicholas D.; Ellis, Keith C.; Chobanian, Harry R. (2005). "Generation of Nonracemic 2-(t-Butyldimethylsilyloxy)-3-butynyllithium from (S)-Ethyl Lactate". Organic Syntheses. 81: 157. doi:10.15227/orgsyn.081.0157.
  5. [5]
    Dondoni, Alessandro; Perrone, Daniela (2000). "Diastereoselective Synthesis of Protected Vicinal Amino Alcohols: (S)-2-[(4s)-n-tert-butoxycarbonyl-2,2-dimethyl-1,3-oxazolidinyl]-2-tert-butyldimethylsiloxyethanal from a Serine-Derived Aldehyde". Organic Syntheses. 77: 78. doi:10.15227/orgsyn.077.0078.
  6. [6]
    "tert-Butyldimethylsilyl ethers".
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