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A long chain alcohol as support in solid phase organic synthesis (Alkohol rantai panjang sebagai penyokong dalam sintesis organik fasa pepejal)
Nurlela Y.a, Minnaard A.J.b, Achmad S.a, Wahyuningrum D.a
a Departement of Chemistry, Bandung Institute of Technology, Indonesia
b Zernike Institute for Advanced Materials, University of Groningen, Netherlands
[vc_row][vc_column][vc_row_inner][vc_column_inner][vc_separator css=”.vc_custom_1624529070653{padding-top: 30px !important;padding-bottom: 30px !important;}”][/vc_column_inner][/vc_row_inner][vc_row_inner layout=”boxed”][vc_column_inner width=”3/4″ css=”.vc_custom_1624695412187{border-right-width: 1px !important;border-right-color: #dddddd !important;border-right-style: solid !important;border-radius: 1px !important;}”][vc_empty_space][megatron_heading title=”Abstract” size=”size-sm” text_align=”text-left”][vc_column_text]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.[/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”Author keywords” size=”size-sm” text_align=”text-left”][vc_column_text][/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”Indexed keywords” size=”size-sm” text_align=”text-left”][vc_column_text]4-aminopyridine,C-100 alcohol support,Thorpe-Ziegler cyclization,Transesterification[/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”Funding details” size=”size-sm” text_align=”text-left”][vc_column_text][/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”DOI” size=”size-sm” text_align=”text-left”][vc_column_text][/vc_column_text][/vc_column_inner][vc_column_inner width=”1/4″][vc_column_text]Widget Plumx[/vc_column_text][/vc_column_inner][/vc_row_inner][/vc_column][/vc_row][vc_row][vc_column][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][/vc_column][/vc_row]