Pyrrolidine-Catalyzed Condensation of Ethyl Diazoacetate to Aldehydes in Water

Abstract

A simple and convenient protocol for the synthesis of α-diazo carbonyl compounds from the condensation of ethyl diazoacetate to aldehydes in water was developed using pyrrolidine as a catalyst.

Keywords:

• Aldol-type reaction
• α-diazo carbonyl compounds
• ethyl diazoacetate
• pyrrolidine
• water

ACKNOWLEDGMENTS

We thank the Council for Scientific and Industrial Research (CSIR) for financial support under the Task Force Project CMM-0005. L. C. thanks the CSIR, India, and T. Ramani thanks the University Grants Commission for providing a senior research fellowship.

Notes

^a All reactions were carried out with 30 mol% catalyst, aldehdye (0.5 mmol), EDA (0.55 mmol), solvent (2 mL).

^b Isolated yields.

^a All reactions were carried out with 30 mol% catalyst, aldehdye (0.5 mmol), EDA (0.55 mmol), H₂O (2 mL).

^b Isolated yields.

^a All reactions were carried out with 30 mol (%) catalyst, aldehyde (0.5 mmol), EDA (0.55 mmol), H₂O (2 mL).

^b Isolated yields.

^a All reactions were carried out with 30 mol (%) catalyst, aldehyde (0.5 mmol), EDA (0.55 mmol), H₂O (2 mL).

^b Isolated yields.