Ethylenation of aldehydes to 3-propanal, propanol and propanoic acid derivatives

Methodology has been developed for the synthesis of 3-propanaldehydes through a five-step process in 11–67% yield from aldehydes. Aldehydes were reacted with Meldrum’s acid through a Knoevenagel condensation to give materials that upon reduction with sodium borohydride and subsequent hydrolysis deca...

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Detalles Bibliográficos
Autores principales: Payne, Daniel T., Zhao, Yiming, Fossey, John S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5431831/
https://www.ncbi.nlm.nih.gov/pubmed/28496208
http://dx.doi.org/10.1038/s41598-017-01950-7
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author Payne, Daniel T.
Zhao, Yiming
Fossey, John S.
author_facet Payne, Daniel T.
Zhao, Yiming
Fossey, John S.
author_sort Payne, Daniel T.
collection PubMed
description Methodology has been developed for the synthesis of 3-propanaldehydes through a five-step process in 11–67% yield from aldehydes. Aldehydes were reacted with Meldrum’s acid through a Knoevenagel condensation to give materials that upon reduction with sodium borohydride and subsequent hydrolysis decarboxylation generated the corresponding 3-propanoic acid derivatives. The -propanoic acid derivatives were reduced to give 3-propanol derivatives, which were readily oxidised to target 3-propanal derivatives.
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spelling pubmed-54318312017-05-16 Ethylenation of aldehydes to 3-propanal, propanol and propanoic acid derivatives Payne, Daniel T. Zhao, Yiming Fossey, John S. Sci Rep Article Methodology has been developed for the synthesis of 3-propanaldehydes through a five-step process in 11–67% yield from aldehydes. Aldehydes were reacted with Meldrum’s acid through a Knoevenagel condensation to give materials that upon reduction with sodium borohydride and subsequent hydrolysis decarboxylation generated the corresponding 3-propanoic acid derivatives. The -propanoic acid derivatives were reduced to give 3-propanol derivatives, which were readily oxidised to target 3-propanal derivatives. Nature Publishing Group UK 2017-05-11 /pmc/articles/PMC5431831/ /pubmed/28496208 http://dx.doi.org/10.1038/s41598-017-01950-7 Text en © The Author(s) 2017 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Payne, Daniel T.
Zhao, Yiming
Fossey, John S.
Ethylenation of aldehydes to 3-propanal, propanol and propanoic acid derivatives
title Ethylenation of aldehydes to 3-propanal, propanol and propanoic acid derivatives
title_full Ethylenation of aldehydes to 3-propanal, propanol and propanoic acid derivatives
title_fullStr Ethylenation of aldehydes to 3-propanal, propanol and propanoic acid derivatives
title_full_unstemmed Ethylenation of aldehydes to 3-propanal, propanol and propanoic acid derivatives
title_short Ethylenation of aldehydes to 3-propanal, propanol and propanoic acid derivatives
title_sort ethylenation of aldehydes to 3-propanal, propanol and propanoic acid derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5431831/
https://www.ncbi.nlm.nih.gov/pubmed/28496208
http://dx.doi.org/10.1038/s41598-017-01950-7
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