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

M. Alex Radtke; Caroline C. Dudley; Jacob M. O’Leary; Tristan H. Lambert

doi:10.1055/s-0037-1611650

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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

^aDepartment of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027, USA

,

Caroline C. Dudley

^bDepartment of Chemistry and Chemical Biology, Cornell University, 259 East Ave, Ithaca, NY 14850, USA Email: Tristan.lambert@cornell.edu

,

Jacob M. O’Leary

^bDepartment of Chemistry and Chemical Biology, Cornell University, 259 East Ave, Ithaca, NY 14850, USA Email: Tristan.lambert@cornell.edu

,

Tristan H. Lambert *

^aDepartment of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027, USA

^bDepartment of Chemistry and Chemical Biology, Cornell University, 259 East Ave, Ithaca, NY 14850, USA Email: Tristan.lambert@cornell.edu

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Abstract

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Published as part of the 50 Years SYNTHESIS – Golden 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.

Key words

Brønsted acid - PCCP - cyclopentadiene - dimethyl malonate - dimethyl acetylenedicarboxylate

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References

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