2-(Trimethylsilyl)ethoxymethyl chloride

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%]