skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Synthesis of a biofuel target through conventional organic chemistry

Abstract

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 the 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 upon workup of the previous step to yield a primarily a mixture of exo diastereomers 9a and 9b in 77% yield. These targets had their fuel properties characterized in a separate study.

Authors:
; ; ;
Publication Date:
Research Org.:
Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1452867
Report Number(s):
PNNL-SA-129880
Journal ID: ISSN 0040-4039; BM0102060
DOE Contract Number:
AC05-76RL01830
Resource Type:
Journal Article
Resource Relation:
Journal Name: Tetrahedron Letters; Journal Volume: 59; Journal Issue: 14
Country of Publication:
United States
Language:
English
Subject:
Biofuel; Organic Synthesis

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. doi:10.1016/j.tetlet.2018.02.073.
Page, Jordan P., Robinson, Joshua W., Albrecht, Karl O., and Cosimbescu, Lelia. Sun . "Synthesis of a biofuel target through conventional organic chemistry". United States. doi:10.1016/j.tetlet.2018.02.073.
@article{osti_1452867,
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 = {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 the 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 upon workup of the previous step to yield a primarily a mixture of exo diastereomers 9a and 9b in 77% yield. These targets had their fuel properties characterized in a separate study.},
doi = {10.1016/j.tetlet.2018.02.073},
journal = {Tetrahedron Letters},
number = 14,
volume = 59,
place = {United States},
year = {Sun Apr 01 00:00:00 EDT 2018},
month = {Sun Apr 01 00:00:00 EDT 2018}
}