1-(Chloromethoxy)-2-methoxyethane

UsesOH-protecting reagent. MEM ethers are stable to a variety of reaction conditions and are selectively cleaved under aprotic conditions in the presence of a wide rangeof OH-protected moieties.

Uses2-Methoxyethoxymethyl Chloride is an OH-protecting reagent. 2-Methoxyethoxymethyl Chloride is used in the modification of antibiotics.

Uses2-Methoxyethoxymethyl chloride, is used as selectively cleaved under aprotic conditions in the presence of a wide range of OH-protected reagents. It is used as an OH-protecting reagent. An examples of the target molecule MEM Chloride is the side chain of roxithromycin. It is also used in the protection of the OH groups in serine and threonine during peptide synthesis. Some of the other applications include have the ability to coordinate to metals, which is thought to accelerate the cleavage by Lewis acids. The chelating ability of the MEM ether also makes it useful as a stereodirecting group in organometallic reactions, first noted in the stereo controlled addition of -methoxyvinyllithium to a carbonyl in the synthesis of taxusin.

Preparation2-Methoxyethoxymethyl chloride can be synthesized by reacting 2-methoxyethanol with thionyl chloride. However, this method has some problems, requiring high temperatures and long reaction times to obtain high yields. Furthermore, thionyl chloride is a toxic substance and is environmentally unfriendly.