2-(Trimethylsilyl)ethoxymethyl chloride

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2-(Trimethylsilyl)ethoxymethyl chloride
2-(Trimethylsilyl)ethoxymethyl chloride.svg
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.071.328 Edit this at Wikidata
EC Number
  • 278-483-4
  • InChI=1S/C6H15ClOSi/c1-9(2,3)5-4-8-6-7/h4-6H2,1-3H3
    Key: BPXKZEMBEZGUAH-UHFFFAOYSA-N
  • C[Si](C)(C)CCOCCl
Properties
C6H15ClOSi
Molar mass 166.72 g·mol−1
Appearance Colorless liquid[1]
Boiling point 57–59 °C (330–332 K) (8 mmHg)[1]
Hazards
GHS labelling:
GHS02: FlammableGHS05: Corrosive
Signal word
 Danger
H226, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2-(Trimethylsilyl)ethoxymethyl chloride (SEM-Cl) is an organochlorine compound with the formula C6H15ClOSi, which was developed by Bruce H. Lipshutz during his work on the synthesis of N-methylmaysenine. It is used to protect hydroxyl group, which can be cleaved with fluoride in organic solvents selectively under mild conditions.[1] Typically tetrabutylammonium fluoride and caesium fluoride can be used as deprotection reagents. Alternatives such as magnesium bromide,[2] lithium tetrafluoroborate and boron trifluoride etherate were also developed to deprotect SEM group.[3]

References[]

  1. ^ a b c Lipshutz, Bruce H.; Pegram, Joseph J. (1980). "β-(Trimethylsilyl)ethoxymethyl chloride. A new reagent for the protection of the hydroxyl group". Tetrahedron Letters. Elsevier BV. 21 (35): 3343–3346. doi:10.1016/s0040-4039(00)78684-9. ISSN 0040-4039.
  2. ^ Vakalopoulos, Alexandros; Hoffmann, H. M. R. (2000-04-21). "Novel Deprotection of SEM Ethers: A Very Mild and Selective Method Using Magnesium Bromide". Organic Letters. American Chemical Society (ACS). 2 (10): 1447–1450. doi:10.1021/ol0057784. ISSN 1523-7060. PMID 10814469.
  3. ^ Katritzky, A.R.; Kirby, G.W.; Meth-Cohn, O.; Rees, C.W. (1995). Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations. Elsevier Science. p. 176. ISBN 978-0-08-042325-8. Retrieved 2021-10-25.

Further reading[]

  • Nair, Reji N.; Bannister, Thomas D. (2016-06-21). "Tale of Two Protecting Groups—Boc vs SEM—for Directed Lithiation and C–C Bond Formation on a Pyrrolopyridazinone Core". Organic Process Research & Development. American Chemical Society (ACS). 20 (7): 1370–1376. doi:10.1021/acs.oprd.6b00128. ISSN 1083-6160.
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