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Benzyl 2,2,2-trichloroacetimidate is used for the acid-catalyzed benzylation of hydroxy groups. It acts as reagent during the synthesis of funiculosin dimethyl ether and (S)-3-(benzyloxy)-2-methylpropanal. It can also be used for mild esterification of carboxylic acids in the presence of a catalytic amount of BF3 etherate.
Mild, selective benzylating agent. Formation of benzyl ethers from alcohols at room temperature is catalyzed by triflic acid; isopropylidene and benzylidene protecting groups are unaffected: J. Chem. Soc., Perkin 1., 2247 (1985). TMS triflate has also been recommended as a catalyst, avoiding racemization of sensitive substrates: Tetrahedron, 43, 1619 (1993). For use in the preparation of benzyl ethers of ß-hydroxy esters, see: Synthesis, 568 (1987).
The reagent can also be used for mild esterification of carboxylic acids in the presence of a catalytic amount of BF3 etherate: Synthesis, 168 (1997). For conversion of N-Boc groups to N-Cbz, catalyzed by triflic acid, see: J. Org. Chem., 55, 5170 (1990). See also Appendix 6.
Chen, T.; Altmann, K. H. Directed Hydrogenations and an Ireland-Claisen Rearrangement Linked to Evans-Tishchenko Chemistry: The Highly Efficient Total Synthesis of the Marine Cyclodepsipeptide Doliculide. Chem. Eur. J 2015, 21 (23), 8403-8407.
Miller, D. C.; Carbain, B.; Beale, G. S.; Alhasan, S. F.; Reeves, H. L.; Baisch, U.; Newell, D. R.; Golding, B. T.; Griffin, R. J. Regioselective sulfamoylation at low temperature enables concise syntheses of putative small molecule inhibitors of sulfatases. Org. Biomol. Chem. 2015, 13 (18), 5279-5284 .
Hazard Statements: H302-H315-H319-H335
Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.