2-(Trimethylsilyl)ethoxymethyl chloride

Chemical properties

Colorless to light yellow liqui

Physical properties

bp 57–59 °C/8 mmHg; d 0.942 g cm?3.

The Uses of 2-(Trimethylsilyl)ethoxymethyl chloride

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.

The Uses of 2-(Trimethylsilyl)ethoxymethyl chloride

To a solution of the SM (270 mg, 1.0 mmol) in THF was added NaH (44 mg, 1.1 mmol) in four portions. The resulting mixture was stirred at RT for 15 min, after which time was added SEM-Cl (0.19 mL, 1.0 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was quenched by the addition of H2O, then diluted with EtOAc. The org layer was separated and the aq layer was further extracted with EtOAc (2x). The combined organics were washed with brine, dried (MgSO4), and concentrated. The resulting material was purified by flash chromatography (eluting with 5-20% EtOAc/heptane) to provide the product as a white solid. [270 mg, 67%]

The Uses of 2-(Trimethylsilyl)ethoxymethyl chloride

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.

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.

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.]