2-(Trimethylsilyl)ethoxymethyl chloride

2-(Trimethylsilyl)ethoxymethyl chloride.svg 200px [2-(Chloromethoxy)ethyl]tri(methyl)silane 76513-69-4 correct CAS correct FDA G8Q8Y64LT8 2006421 278-483-4 2724271 1S/C6H15ClOSi/c1-9(2,3)5-4-8-6-7/h4-6H2,1-3H3 BPXKZEMBEZGUAH-UHFFFAOYSA-N C[Si](C)(C)CCOCCl 6 15 1 1 1 Colorless liquid 57 - 59 C K (8 mmHg) 02 05 Danger 226 314 210 233 240 241 242 243 260 264 280 301+330+331 303+361+353 304+340 305+351+338 310 321 363 370+378 403+235 405 501 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 groups, which can be cleaved with fluoride in organic solvents selectively under mild conditions.Lipshutz Bruce H. Pegram Joseph J. β-(Trimethylsilyl)ethoxymethyl chloride. A new reagent for the protection of the hydroxyl group Tetrahedron Letters Elsevier BV 21 35 1980 0040-4039 10.1016/s0040-4039(00)78684-9 3343–3346 Typically tetrabutylammonium fluoride and caesium fluoride can be used as deprotection reagents. Alternatives such as magnesium bromide,Vakalopoulos Alexandros Hoffmann H. M. R. Novel Deprotection of SEM Ethers: A Very Mild and Selective Method Using Magnesium Bromide Organic Letters American Chemical Society (ACS) 2 10 2000-04-21 1523-7060 10.1021/ol0057784 1447–1450 10814469 lithium tetrafluoroborate and boron trifluoride etherate were also developed to deprotect SEM group.Katritzky A.R. Kirby G.W. Meth-Cohn O. Rees C.W. Comprehensive Organic Functional Group Transformations Elsevier Science v. 4 1995 978-0-08-042325-8 https://books.google.com/books?id=0RQEsfYCuBcC&pg=PA176 2021-10-25 176 References Further reading Nair Reji N. Bannister Thomas D. 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 2016-06-21 1083-6160 10.1021/acs.oprd.6b00128 1370–1376 Category:Chloromethyl compounds Category:Trimethylsilyl compounds