3-Nitrobenzeneboronic Acid as an Efficient and Environmentally Benign Catalyst for the Selective Transesterification of β-Keto Esters

Abstract

An efficient and high-yielding procedure for the selective transesterification of various β-keto esters using 3-nitrobenzeneboronic acid as a catalyst in an environmentally acceptable process is described.

Key words

β-keto esters - 3-nitrobenzeneboronic acid - environmentally benign - selective reaction

References and Notes

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21

Typical Procedure (Table 1, entry 8): Ethyl acetoacetate (5 mmol), 3-nitrobenzyl alcohol (5 mmol) and 3-nitro-benzeneboronic acid (21 mg, 2.5 mol%) in 20 mL of toluene was heated at reflux for the time allotted (Table [1] ) with removal of toluene-ethanol azeotrope by distillation. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was concentrated and the residue was chromatographed on silica gel (elution with EtOAc-hexane; 20:80) to afford the pure 3-nitrobenzyl acetoacetate.