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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Universiti Kebangsaan Malaysia
2011
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| Online Access: | http://journalarticle.ukm.my/2629/ http://journalarticle.ukm.my/2629/ http://journalarticle.ukm.my/2629/1/05_Yeni.pdf |
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ukm-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/ |
| repository_type |
Digital Repository |
| institution_category |
Local University |
| institution |
Universiti Kebangasaan Malaysia |
| building |
UKM Institutional Repository |
| collection |
Online Access |
| 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/ http://journalarticle.ukm.my/2629/ http://journalarticle.ukm.my/2629/1/05_Yeni.pdf |
| first_indexed |
2023-09-18T19:36:35Z |
| last_indexed |
2023-09-18T19:36:35Z |
| _version_ |
1777405311710134272 |