85695-26-7Relevant academic research and scientific papers
Trichloromethyltrimethylsilane, sodium formate, and dimethylformamide: A mild, efficient, and general method for the preparation of trimethylsilyl- protected 2,2,2-trichloromethylcarbinols from aldehydes and ketones
Kister, Jeremy,Mioskowski, Charles
, p. 3925 - 3928 (2007)
(Chemical Equation Presented) New conditions for the preparation of trimethylsilyl-protected 2,2,2-trichloromethylcarbinols 2 from aldehydes and ketones are reported. Compounds 2, which are important intermediates in organic synthesis, were obtained in excellent yields by use of a combination of trichloromethyltrimethylsilane (TMSCCI3), and a catalytic amount of sodium formate (HCOONa) in dimethylformamide (DMF). Substrates bearing highly sensitive protecting groups have been successfully subjected to our conditions. We also describe a one-pot procedure that gives direct access to 2,2,2-trichloromethylcarbinols 3. This methodology avoids the use of strong bases usually required for the synthesis of 3 (Wyvratt et al. J. Org. Chem. 1987, 52, 944; Aggarwal and Mereu, J. Org. Chem. 2000, 65, 7211).
TRIMETHYLSILYL TRICHLOROACETATE: A NEW REAGENT FOR SALT-FREE SILYLATIONS
Renga, James M.,Pen-Chung, Wang
, p. 1175 - 1178 (2007/10/02)
Trimethylsylil trichloroacetate (1) is a convenient reagent for the silylation of phenols, carboxylic acids, mercaptans, amides, acetylenes, and β-keto esters, while the reaction of 1 with aldehydes and ketones affords silylated trichloromethyl carbinols (5).
