Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones

The one-pot cyclization of 5-hexynoic acid to produce 3-alkoxy-2-cyclohexenones proceeds in good yields (58–90%). 3-Hexynoic acid was converted to its acyl chloride with the aid of oxalyl chloride and was cyclized to 3-chloro-2-cyclohexenone upon addition of indium(III) chloride. Subsequent addition...

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Autores principales: Hylden, Anne T, Uzelac, Eric J, Ostojic, Zeljko, Wu, Ting-Ting, Sacry, Keely L, Sacry, Krista L, Xi, Lin, Jones, T Nicholas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201045/
https://www.ncbi.nlm.nih.gov/pubmed/22043242
http://dx.doi.org/10.3762/bjoc.7.155
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author Hylden, Anne T
Uzelac, Eric J
Ostojic, Zeljko
Wu, Ting-Ting
Sacry, Keely L
Sacry, Krista L
Xi, Lin
Jones, T Nicholas
author_facet Hylden, Anne T
Uzelac, Eric J
Ostojic, Zeljko
Wu, Ting-Ting
Sacry, Keely L
Sacry, Krista L
Xi, Lin
Jones, T Nicholas
author_sort Hylden, Anne T
collection PubMed
description The one-pot cyclization of 5-hexynoic acid to produce 3-alkoxy-2-cyclohexenones proceeds in good yields (58–90%). 3-Hexynoic acid was converted to its acyl chloride with the aid of oxalyl chloride and was cyclized to 3-chloro-2-cyclohexenone upon addition of indium(III) chloride. Subsequent addition of alcohol nucleophiles led to the desired 3-alkoxy-2-cyclohexenones.
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spelling pubmed-32010452011-10-31 Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones Hylden, Anne T Uzelac, Eric J Ostojic, Zeljko Wu, Ting-Ting Sacry, Keely L Sacry, Krista L Xi, Lin Jones, T Nicholas Beilstein J Org Chem Letter The one-pot cyclization of 5-hexynoic acid to produce 3-alkoxy-2-cyclohexenones proceeds in good yields (58–90%). 3-Hexynoic acid was converted to its acyl chloride with the aid of oxalyl chloride and was cyclized to 3-chloro-2-cyclohexenone upon addition of indium(III) chloride. Subsequent addition of alcohol nucleophiles led to the desired 3-alkoxy-2-cyclohexenones. Beilstein-Institut 2011-09-23 /pmc/articles/PMC3201045/ /pubmed/22043242 http://dx.doi.org/10.3762/bjoc.7.155 Text en Copyright © 2011, Hylden et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Hylden, Anne T
Uzelac, Eric J
Ostojic, Zeljko
Wu, Ting-Ting
Sacry, Keely L
Sacry, Krista L
Xi, Lin
Jones, T Nicholas
Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones
title Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones
title_full Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones
title_fullStr Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones
title_full_unstemmed Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones
title_short Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones
title_sort cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201045/
https://www.ncbi.nlm.nih.gov/pubmed/22043242
http://dx.doi.org/10.3762/bjoc.7.155
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