Synthesis of a biofuel target through conventional organic chemistry
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.
- Research Organization:
- Pacific Northwest National Laboratory (PNNL), Richland, WA (US)
- Sponsoring Organization:
- USDOE
- DOE Contract Number:
- AC05-76RL01830
- OSTI ID:
- 1452867
- Report Number(s):
- PNNL-SA-129880; BM0102060
- Journal Information:
- Tetrahedron Letters, Journal Name: Tetrahedron Letters Journal Issue: 14 Vol. 59; ISSN 0040-4039
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- English
Similar Records
Nickel-promoted steroselective cyclization of 1,3-diene and carbonyl group. Effect of 1,3-diene as a ligand