Synthesis of a biofuel target through conventional organic chemistry
Abstract
Here in this work, the biofuel target compound 2-ethyl-5,5-dimethylcyclopenta-1,3-diene (1) and its exo isomers (9a and 9b), were successfully synthesized via two different pathways from the common intermediate 4,4-dimethylcyclopent-2-ene-1-one (2). The first pathway produced the endocyclic product as a pure isomer via a triflate intermediate obtained from ketone 2 in 60% yield, followed by copper-catalyzed coupling with ethyl magnesium bromide in 63% yield. The second pathway employed a Grignard reaction with ketone 2, which generated an alcohol that was immediately subjected to mild acid-catalyzed elimination to yield primarily a mixture of exo isomers 9a and 9b in 46% yield. The preparation method developed by this work allowed for the production of a sufficient quantity of these targets to evaluate their fuel properties, which will be reported in a separate study.
- Authors:
-
- Pacific Northwest National Lab. (PNNL), Richland, WA (United States). Energy and Environment Directorate
- Publication Date:
- Research Org.:
- Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
- Sponsoring Org.:
- USDOE Office of Energy Efficiency and Renewable Energy (EERE), Sustainable Transportation Office. Bioenergy Technologies Office; USDOE Office of Energy Efficiency and Renewable Energy (EERE), Vehicle Technologies Office (EE-3V)
- OSTI Identifier:
- 1423329
- Report Number(s):
- PNNL-S-129880
Journal ID: ISSN 0040-4039; PII: S0040403918302739
- Grant/Contract Number:
- AC0576RL01830
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Tetrahedron Letters
- Additional Journal Information:
- Journal Volume: 2018; Related Information: © 2018 Elsevier Ltd. All rights reserved.; Journal ID: ISSN 0040-4039
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 09 BIOMASS FUELS; Divergent synthesis; Grignard cross-coupling; Alkenes; Biofuels; Cyclopentadiene
Citation Formats
Page, Jordan P., Robinson, Joshua W., Albrecht, Karl O., and Cosimbescu, Lelia. Synthesis of a biofuel target through conventional organic chemistry. United States: N. p., 2018.
Web. doi:10.1016/j.tetlet.2018.02.073.
Page, Jordan P., Robinson, Joshua W., Albrecht, Karl O., & Cosimbescu, Lelia. Synthesis of a biofuel target through conventional organic chemistry. United States. https://doi.org/10.1016/j.tetlet.2018.02.073
Page, Jordan P., Robinson, Joshua W., Albrecht, Karl O., and Cosimbescu, Lelia. Wed .
"Synthesis of a biofuel target through conventional organic chemistry". United States. https://doi.org/10.1016/j.tetlet.2018.02.073. https://www.osti.gov/servlets/purl/1423329.
@article{osti_1423329,
title = {Synthesis of a biofuel target through conventional organic chemistry},
author = {Page, Jordan P. and Robinson, Joshua W. and Albrecht, Karl O. and Cosimbescu, Lelia},
abstractNote = {Here in this work, the biofuel target compound 2-ethyl-5,5-dimethylcyclopenta-1,3-diene (1) and its exo isomers (9a and 9b), were successfully synthesized via two different pathways from the common intermediate 4,4-dimethylcyclopent-2-ene-1-one (2). The first pathway produced the endocyclic product as a pure isomer via a triflate intermediate obtained from ketone 2 in 60% yield, followed by copper-catalyzed coupling with ethyl magnesium bromide in 63% yield. The second pathway employed a Grignard reaction with ketone 2, which generated an alcohol that was immediately subjected to mild acid-catalyzed elimination to yield primarily a mixture of exo isomers 9a and 9b in 46% yield. The preparation method developed by this work allowed for the production of a sufficient quantity of these targets to evaluate their fuel properties, which will be reported in a separate study.},
doi = {10.1016/j.tetlet.2018.02.073},
journal = {Tetrahedron Letters},
number = ,
volume = 2018,
place = {United States},
year = {2018},
month = {2}
}
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