CAS 83766-88-5, Cat. No EN300-7409774
Reagent for carboxylic acids protection
2-tert-Butoxypyridine is a practical tert-butylating agent for tert-butyl ester formation1. When combined with BF3·OEt2, it efficiently protects carboxylic acids under mild conditions. The scope of reaction includes a wide range of carboxylic acids—including aromatic (with electron-donating or electron-withdrawing groups), aliphatic, bulky, cyclic, unsaturated, heteroaryl, and amino acid derivatives. Even sensitive substrates, like furoic acid, give excellent yields without decomposition. The main advantages of the reagent are that it provides mild, fast, and high-yielding esterification suitable for acid-sensitive functional groups and without the use of harsh strong acids (e.g., H2SO4, CF3COOH) or hazardous gases (isobutylene).
Synonyms: 2-tert-butoxypyridine; 2-(tert-butoxy)pyridine; 2-[(2-methylpropan-2-yl)oxy]pyridine
Selected publication
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Fast and Practical Synthesis of Tert-Butyl Esters from 2-Tert-Butoxypyridine Using Boron Trifluoride·diethyl Etherate under Mild Conditions.
La, M. T.; Kim, H. K. A Tetrahedron 2018, 74 (27), 3748–3754. DOI: 10.1016/j.tet.2018.05.050