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Title: Synthesis of a biofuel target through conventional organic chemistry

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:
 [1] ;  [1] ;  [1] ;  [1]
  1. Pacific Northwest National Lab. (PNNL), Richland, WA (United States). Energy and Environment Directorate
Publication Date:
Report Number(s):
PNNL-S-129880
Journal ID: ISSN 0040-4039; PII: S0040403918302739
Grant/Contract Number:
AC0576RL01830
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
Research Org:
Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Sponsoring Org:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Bioenergy Technologies Office (EE-3B); USDOE Office of Energy Efficiency and Renewable Energy (EERE), Vehicle Technologies Office (EE-3V)
Country of Publication:
United States
Language:
English
Subject:
09 BIOMASS FUELS; Divergent synthesis; Grignard cross-coupling; Alkenes; Biofuels; Cyclopentadiene
OSTI Identifier:
1423329

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., 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. doi:10.1016/j.tetlet.2018.02.073.
Page, Jordan P., Robinson, Joshua W., Albrecht, Karl O., and Cosimbescu, Lelia. 2018. "Synthesis of a biofuel target through conventional organic chemistry". United States. doi:10.1016/j.tetlet.2018.02.073.
@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}
}