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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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.