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TMSCl is reactive toward nucleophiles, resulting in the replacement of the chloride. In a characteristic reaction of TMSCl, the nucleophile is water, resulting in hydrolysis to give the hexamethyldisiloxane: + + The related reaction of trimethylsilyl chloride with alcohols can be exploited to produce anhydrous solutions of hydrochloric acid in alcohols, which find use in the mild synthesis of ...
When attached to certain functional groups in a reactant molecule, trimethylsilyl groups may also be used as temporary protecting groups during chemical synthesis or some other chemical reactions. In chromatography, derivitization of accessible silanol groups in a bonded stationary phase with trimethylsilyl groups is referred to as endcapping.
One reliable and rapid procedure is the Corey protocol in which the alcohol is reacted with a silyl chloride and imidazole at high concentration in DMF. [1] If DMF is replaced by dichloromethane, the reaction is somewhat slower, but the purification of the compound is simplified. A common hindered base for use with silyl triflates is 2,6 ...
Trimethylsilyl chloride, activated with imidazole, protects a secondary alcohol. Triorganosilyl sources have quite variable prices, and the most economical is chlorotrimethylsilane (TMS-Cl), a Direct Process byproduct.
The protection mechanism begins with the base deprotonating the alcohol group. Next, the deprotonated alcohol group attacks the silyl atom of the silyl halide compound. The halide acts as a leaving group and ends up in solution. A workup step follows to remove any excess base within the solution. The overall reaction scheme is as follows:
The methylchlorosilanes react with water to produce hydrogen chloride, giving siloxanes. In the case of trimethylsilyl chloride, the hydrolyzed product is hexamethyldisiloxane: 2 ((CH 3) 3 SiCl + H 2 O → [(CH 3) 3 Si] 2 O + 2 HCl. The analogous reaction of dimethyldichlorosilane gives siloxane polymers or rings: n (CH 3) 2 SiCl 2 + n H 2 O ...
As such it is more bulky that trimethylsilyl chloride. It is a colorless or white solid that is soluble in many organic solvents but reacts with water and alcohols. The compound is used to protect alcohols in organic synthesis. [1] tert-Butyldimethylsilyl chloride reacts with alcohols in the presence of base to give tert-butyldimethylsilyl ...
Hexamethyldisiloxane can be produced by the addition of trimethylsilyl chloride to purified water: 2 Me 3 SiCl + H 2 O → 2 HCl + O[Si(CH 3) 3] 2. It also results from the hydrolysis of silyl ethers and other silyl-protected functional groups. HMDSO can be converted back to the chloride by reaction with Me 2 SiCl 2. [3]