CC BY-ND-NC 4.0 · Synthesis 2019; 51(05): 1135-1138
DOI: 10.1055/s-0037-1611650
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A Scalable, One-Pot Synthesis of 1,2,3,4,5-Pentacarbomethoxycyclopentadiene

M. Alex Radtke
a  Department of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027, USA
,
Caroline C. Dudley
b  Department of Chemistry and Chemical Biology, Cornell University, 259 East Ave, Ithaca, NY 14850, USA   Email: Tristan.lambert@cornell.edu
,
Jacob M. O’Leary
b  Department of Chemistry and Chemical Biology, Cornell University, 259 East Ave, Ithaca, NY 14850, USA   Email: Tristan.lambert@cornell.edu
,
a  Department of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027, USA
b  Department of Chemistry and Chemical Biology, Cornell University, 259 East Ave, Ithaca, NY 14850, USA   Email: Tristan.lambert@cornell.edu
› Author Affiliations
This work is supported by the NIH (R35 GM127135). This work made use of the Cornell University NMR Facility, which is supported, in part, by the NSF through MRI award CHE-1531632.
Further Information

Publication History

Received: 07 December 2018

Accepted: 14 December 2018

Publication Date:
22 January 2019 (online)

Published as part of the 50 Years SYNTHESISGolden Anniversary Issue

Abstract

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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