Methylsilyl trifluoromethanesulfonate

ALDOL CONDENSATION Cesium fluoride. Dialkylboron trifluoromethane-sulfonates. Dichlorobis(cyclopentadi-enyl)zirconium. Diisobutylaluminum phenoxide. 2,5-Dimethylphenylpropi-onate. DimetIiyl(phenyllhio)aIuminum. Lithium iodide. Triethylborane. Tri-methylsilyl trifluoromethanesulfonate. Triphenyltin chloride. TrisCdiethyI-amino)sulfonium difluorotrimethyl-siliconate. 

Silver trifluoromethanesulfonate, methylsilyl trifluoromethanesulfonate, dime-thylmethylthiosulfonium-trifluoromethane sulfonate (DMTST), and boron trifluoride diethyl etherate were obtained from Sigma-Aldrich. 

SILYLATION Allyltrimethylsilane. Bistri-methylsilyl ether. 4-(f-Butyldimethyl-silyloxy-3-pentene-2-one. /-Butyldi-methylsilyl trifluoromethanesulfonate. Chloromethyldiphenylsilane. Chlorotri-methylsilane. Hexamethyldisiloxane. 

Related Reagents. t-Butyldimethylchlorosilane r-Butyldi-methylsilyl Trifluoromethanesulfonate Chlorotriphenylsilane Triisopropylsilyl Chloride. 

One-carbon Homologation of Carboxylic Acids. l-[(Tri-methylsilyl)methyl]benzotriazole converts benzoyl chlorides to the corresponding (benzotriazol-l-yl)methyl aryl ketones in high yields (see eq 1). Treatment with triflic anhydride and 2,6-lutidine in CH2CI2 converts these ketones into their enolate triflates in 83-95% yields (eq 4). In the subsequent steps, the triflates are treated with sodium methoxide and then with ethanolic HCl to afford ethyl esters of the corresponding arylacetic acids in 89-98% yields (eq 5). The proposed reaction mechanism involves elimination of trifluoromethanesulfonic acid with sodium methoxide and final alcoholysis of the obtained l-(arylethynyl)benzotriazole intermediates with ethanolic HCl. A comparable classical method for one-carbon homologation of carboxylic acids, the Amdt-Eistert reaction, involves difficult to handle diazomethane and Q -diazoketones. ... 

Related Reagents. r-Butyldimethylchlorosilane N-(t-Butyldimethylsilyl)-Af-methyltrifluoroacetamide r-Butyldi-methylsilyl Perchlorate Triethyl Trifluoromethanesulfonate Trimethylsilyl Trifluoromethanesulfonate. 

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