Recently, 2-(Trimethylsilyl)ethoxymethyl chloride (SEM-Cl), a commonly used protecting agent for amino and hydroxyl groups in heterocyclic compounds, has garnered widespread attention in the field of organic synthesis due to its efficient protection and deprotection properties. This reagent is a colorless, clear liquid with the molecular formula C6H15ClOSi, molecular weight 166.72, CAS number 76513-69-4, melting point 57-59℃, and should be hermetically stored in a dry, well-ventilated environment at -20℃.
    Common bases for SEM-Cl protection reactions include potassium carbonate, sodium hydride (NaH), etc., with NaH being the most widely used. In a typical experiment, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine is used as the starting material, SEM-Cl is added to the dry DMF and NaH system, and the yield can reach 76% after purification by column chromatography. Deprotection adopts a two-step method: first removing the trimethylsilylethyl group under acidic conditions, then removing the hydroxymethyl group under basic conditions, providing an efficient solution for the synthesis of heterocyclic compounds. Relevant research results have been published in the journal Molecules, offering important technical support for fields such as drug synthesis and material chemistry.

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