Synthesis of benzyl esters using 2-benzyloxy-1-methylpyridinium triflate.
Triethylamine (Et3N) mediates esterification reactions between the title reagent (1) and carboxylic acids. Alcohols, phenols, amides, and other sensitive functionality are not affected; a dual role for Et3N as a promoter and a scavenger is postulated. Benzyl esters are obtained from substrates including amino acid and sugar derivatives.
Tummatorn
Jumreang
J
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA.
Albiniak
Philip A
PA
Dudley
Gregory B
GB
D002264:Carboxylic Acids / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D011726:Pyridinium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
C525419:2-benzyloxy-1-methylpyridinium triflate; D002264:Carboxylic Acids; D004952:Esters; D008698:Mesylates; D011726:Pyridinium Compounds