Preparation of adamantylidene enol ethers by Wittig-Horner reaction

A practical synthetic pathway of adamantylidene enol ethers by Wittig-Horner reaction has been developed. In this route, acetals were obtained by reaction of trimethyl orthoformate and benzaldehyde derivatives with tetrabutylammonium tribromide in methanol at room temperature. Trimethyl phosphite wa...

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Autores principales:	Xinxin Huang, Chun Cai
Formato:	article
Lenguaje:	EN
Publicado:	Elsevier 2021
Materias:	Adamantylidene enol ether Wittig-Horner reaction 2-adamantanone Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/f2ae106aee5a4b8eb897fee95a55a365
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spelling	oai:doaj.org-article:f2ae106aee5a4b8eb897fee95a55a3652021-11-14T04:32:35ZPreparation of adamantylidene enol ethers by Wittig-Horner reaction2211-715610.1016/j.rechem.2021.100238https://doaj.org/article/f2ae106aee5a4b8eb897fee95a55a3652021-01-01T00:00:00Zhttp://www.sciencedirect.com/science/article/pii/S2211715621001430https://doaj.org/toc/2211-7156A practical synthetic pathway of adamantylidene enol ethers by Wittig-Horner reaction has been developed. In this route, acetals were obtained by reaction of trimethyl orthoformate and benzaldehyde derivatives with tetrabutylammonium tribromide in methanol at room temperature. Trimethyl phosphite was converted into phosphonates with acetals in the presence of titanium (Ⅳ) tetrachloride in dichloromethane, followed by utilization of 2-adamantanone and lithium diisopropylamide (LDA) in anhydrous tetrahydrofuran under argon atmosphere at −78 °C to form adamantylidene enol ethers. Total yields are up to 66%.Xinxin HuangChun CaiElsevierarticleAdamantylidene enol etherWittig-Horner reaction2-adamantanoneChemistryQD1-999ENResults in Chemistry, Vol 3, Iss , Pp 100238- (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Adamantylidene enol ether Wittig-Horner reaction 2-adamantanone Chemistry QD1-999
spellingShingle	Adamantylidene enol ether Wittig-Horner reaction 2-adamantanone Chemistry QD1-999 Xinxin Huang Chun Cai Preparation of adamantylidene enol ethers by Wittig-Horner reaction
description	A practical synthetic pathway of adamantylidene enol ethers by Wittig-Horner reaction has been developed. In this route, acetals were obtained by reaction of trimethyl orthoformate and benzaldehyde derivatives with tetrabutylammonium tribromide in methanol at room temperature. Trimethyl phosphite was converted into phosphonates with acetals in the presence of titanium (Ⅳ) tetrachloride in dichloromethane, followed by utilization of 2-adamantanone and lithium diisopropylamide (LDA) in anhydrous tetrahydrofuran under argon atmosphere at −78 °C to form adamantylidene enol ethers. Total yields are up to 66%.
format	article
author	Xinxin Huang Chun Cai
author_facet	Xinxin Huang Chun Cai
author_sort	Xinxin Huang
title	Preparation of adamantylidene enol ethers by Wittig-Horner reaction
title_short	Preparation of adamantylidene enol ethers by Wittig-Horner reaction
title_full	Preparation of adamantylidene enol ethers by Wittig-Horner reaction
title_fullStr	Preparation of adamantylidene enol ethers by Wittig-Horner reaction
title_full_unstemmed	Preparation of adamantylidene enol ethers by Wittig-Horner reaction
title_sort	preparation of adamantylidene enol ethers by wittig-horner reaction
publisher	Elsevier
publishDate	2021
url	https://doaj.org/article/f2ae106aee5a4b8eb897fee95a55a365
work_keys_str_mv	AT xinxinhuang preparationofadamantylideneenolethersbywittighornerreaction AT chuncai preparationofadamantylideneenolethersbywittighornerreaction
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Preparation of adamantylidene enol ethers by Wittig-Horner reaction

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