A Scalable, One-Pot Synthesis of 1,2,3,4,5-Pentacarbomethoxycyclopentadiene.

Synthesis (Stuttg)

Department of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027, USA.

Published: March 2019

1,2,3,4,5-Pentacarbomethoxycyclopentadiene (PCCP) is a strong organic acid and a precursor to useful organocatalysts, including chiral Brønsted acids and silicon-based Lewis acids. The synthetic route to PCCP, first reported in 1942, is inconvenient for a number of reasons. The two-step synthesis requires the purification of intermediates from intractable side-products, high reaction temperatures, and extensive labor (3 days). We have developed an improved procedure that delivers PCCP efficiently in 24 hours in one pot at ambient temperature and without isolation.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6498842PMC
http://dx.doi.org/10.1055/s-0037-1611650DOI Listing

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