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A long chain alcohol as support in solid phase organic synthesis

The solid phase synthesis is a method by which organic compound synthesis are performed on a support. With this method, the purification can be carried out easily by simple filtration and washing procedures. Long-chain alcohol (C-100 alcohol) can be used as a support because of its insolubility in o...

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Main Authors: Yeni Nurlela,, Adrian J. Minnaard,, Sadijah Achmad,, Deana Wahyuningrum,
Format: Article
Language:English
Published: Universiti Kebangsaan Malaysia 2011
Online Access:http://journalarticle.ukm.my/2629/1/05_Yeni.pdf
http://journalarticle.ukm.my/2629/
http:www.ukm.my/jsm/
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spelling my-ukm.journal.26292016-12-14T06:32:11Z http://journalarticle.ukm.my/2629/ A long chain alcohol as support in solid phase organic synthesis Yeni Nurlela, Adrian J. Minnaard, Sadijah Achmad, Deana Wahyuningrum, The solid phase synthesis is a method by which organic compound synthesis are performed on a support. With this method, the purification can be carried out easily by simple filtration and washing procedures. Long-chain alcohol (C-100 alcohol) can be used as a support because of its insolubility in organic solvents and its simple structure which enables it to be stable in various reaction conditions. In this study, a 4-aminopyridine derivative has been synthesized from C-100 β-keto ester and a cyano enamine using tin(VI)chloride as catalyst. C-100 β-keto ester was obtained by transesterification of long chain alcohol (the support) with ethyl acetoacetate using boric acid protocol. The cyano enamine was successfully synthesized by Thorpe-Ziegler cyclization initiated by sodium hydride. The 4-aminopyridine derivative was successfully cleaved from the support using sodium isopropoxide in refluxing isopropanol. From the 1H-NMR spectrum at ~ 120oC, it was found that the cleaved support has the same spectrum with the long-chain alcohol used in the beginning of reaction, thus, this long chain alcohol can be reused for other reactions Universiti Kebangsaan Malaysia 2011-09 Article PeerReviewed application/pdf en http://journalarticle.ukm.my/2629/1/05_Yeni.pdf Yeni Nurlela, and Adrian J. Minnaard, and Sadijah Achmad, and Deana Wahyuningrum, (2011) A long chain alcohol as support in solid phase organic synthesis. Sains Malaysiana, 40 (9). pp. 977-983. ISSN 0126-6039 http:www.ukm.my/jsm/
institution Universiti Kebangsaan Malaysia
building Perpustakaan Tun Sri Lanang Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Kebangsaan Malaysia
content_source UKM Journal Article Repository
url_provider http://journalarticle.ukm.my/
language English
description The solid phase synthesis is a method by which organic compound synthesis are performed on a support. With this method, the purification can be carried out easily by simple filtration and washing procedures. Long-chain alcohol (C-100 alcohol) can be used as a support because of its insolubility in organic solvents and its simple structure which enables it to be stable in various reaction conditions. In this study, a 4-aminopyridine derivative has been synthesized from C-100 β-keto ester and a cyano enamine using tin(VI)chloride as catalyst. C-100 β-keto ester was obtained by transesterification of long chain alcohol (the support) with ethyl acetoacetate using boric acid protocol. The cyano enamine was successfully synthesized by Thorpe-Ziegler cyclization initiated by sodium hydride. The 4-aminopyridine derivative was successfully cleaved from the support using sodium isopropoxide in refluxing isopropanol. From the 1H-NMR spectrum at ~ 120oC, it was found that the cleaved support has the same spectrum with the long-chain alcohol used in the beginning of reaction, thus, this long chain alcohol can be reused for other reactions
format Article
author Yeni Nurlela,
Adrian J. Minnaard,
Sadijah Achmad,
Deana Wahyuningrum,
spellingShingle Yeni Nurlela,
Adrian J. Minnaard,
Sadijah Achmad,
Deana Wahyuningrum,
A long chain alcohol as support in solid phase organic synthesis
author_facet Yeni Nurlela,
Adrian J. Minnaard,
Sadijah Achmad,
Deana Wahyuningrum,
author_sort Yeni Nurlela,
title A long chain alcohol as support in solid phase organic synthesis
title_short A long chain alcohol as support in solid phase organic synthesis
title_full A long chain alcohol as support in solid phase organic synthesis
title_fullStr A long chain alcohol as support in solid phase organic synthesis
title_full_unstemmed A long chain alcohol as support in solid phase organic synthesis
title_sort long chain alcohol as support in solid phase organic synthesis
publisher Universiti Kebangsaan Malaysia
publishDate 2011
url http://journalarticle.ukm.my/2629/1/05_Yeni.pdf
http://journalarticle.ukm.my/2629/
http:www.ukm.my/jsm/
_version_ 1643735442822004736
score 13.211869

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