Chemical Properties
Colorless to light yellow liqui
Physical properties
bp 57–59 °C/8 mmHg; d 0.942 g cm3.
Uses
2-(Chloromethoxy)ethyltrimethylsilane is used in the preparation of SEM [2-(trimethylsilyl)ethoxy]methyl]-ethers. It serves as a phenol protecting group in the synthesis of laterifluorones. Further, it reacts with 1H-imidazole to prepare 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole.
Uses
2-(Trimethylsilyl)ethoxymethyl Chloride is a reagent used in the protection of alcohols, secondary aryl amines, and imidazole,
indole, and pyrrole nitrogens;electrophilic formaldehyde
equivalent; acyl anion equivalent,used in One-carbon Homologations, Cyclizations etc.
General Description
2-(Trimethylsilyl)ethoxymethyl chloride (SEM-Cl) is a widely used reagent for the preparation protection groups for amines, alcohols, phenols, and carboxy groups. The nitrogen of amides and sulfonamides groups are also protected by using SEM-Cl reagent.
Synthesis
Step 4: Take a small amount of intermediate reagent and place it in the reactor, heat to reflux and maintain reflux for 4 hours. After completion of the reaction, cool to 20°C and slowly add trimethylchlorosilane dropwise. During the dropwise addition, the temperature of the solution was gradually increased. Step 5: At the end of the reaction, desorption operation was carried out, controlling the temperature of the depressurized reactor not to exceed 40°C. The residual system residue was dissolved to form a viscous substance, and ethanol was added slowly until no bubbles were generated, and the waste was disposed of. Finally, the solution obtained by desolventization is distilled to collect 2-(trimethylsilyl)ethoxymethyl chloride with a purity of more than 99%.
Purification Methods
Dissolve SEMCl in pentane, dry it (MgSO4), evaporate and distil the residual oil in a vacuum. Stabilise it with 10ppm of diisopropylamine. Store it under N2 in a sealed container in a refrigerator. [Lipshutz & Pegram Tetrahedron Lett 21 3343 1980.]
References
[1] Patent: CN103408576, 2016, B. Location in patent: Paragraph 0020; 0021; 0025
[2] Patent: CN108409776, 2018, A. Location in patent: Page/Page column 5-7
