2-(Trimethylsilyl)ethoxymethyl chloride (SEM-Cl) is an

organochlorine compound An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalent bond, covalently bonded atom of chlorine. The chloroalkane class (alkanes with one or more hydrogens subst ...

with the formula C₆H₁₅ClOSi, which was developed by

Bruce H. Lipshutz Bruce H. Lipshutz (born 1951) is an American chemist. He is a professor at the University of California, Santa Barbara. Biography Lipshutz received his undergraduate degree in chemistry from Binghamton University in 1973. His graduate work was supe ...

during his work on the synthesis of ''N''-methylmaysenine. It is used to protect hydroxyl group, which can be cleaved with

fluoride Fluoride (). According to this source, is a possible pronunciation in British English. is an inorganic, monatomic anion of fluorine, with the chemical formula (also written ), whose salts are typically white or colorless. Fluoride salts typ ...

in organic solvents selectively under mild conditions. Typically

tetrabutylammonium fluoride Tetra-''n''-butylammonium fluoride, commonly abbreviated to TBAF and ''n''-Bu4NF, is a quaternary ammonium salt with the chemical formula (CH3CH2CH2CH2)4N+F−. It is commercially available as the white solid trihydrate and as a solution in tetra ...

and

caesium fluoride Caesium fluoride or cesium fluoride is an inorganic compound with the formula CsF and it is a hygroscopic white salt. Caesium fluoride can be used in organic synthesis as a source of the fluoride anion. Caesium also has the highest electroposit ...

can be used as deprotection reagents. Alternatives such as

magnesium bromide Magnesium bromide is a chemical compound of magnesium and bromine, with the chemical formula . It is white and deliquescent crystalline solid. It is often used as a mild sedative and as an anticonvulsant for treatment of nervous disorders. It is ...

lithium tetrafluoroborate Lithium tetrafluoroborate is an inorganic compound with the formula Li BF4. It is a white crystalline powder. It has been extensively tested for use in commercial secondary batteries, an application that exploits its high solubility in nonpolar ...

and

boron trifluoride Boron trifluoride is the inorganic compound with the formula BF3. This pungent, colourless, and toxic gas forms white fumes in moist air. It is a useful Lewis acid and a versatile building block for other boron compounds. Structure and bondin ...

etherate were also developed to deprotect SEM group.

References

Further reading