Please use this identifier to cite or link to this item:
Title: Convenient synthesis of (<i>E</i>)-methyl <i>O</i>-alkylferulates: Formal synthesis of <i>O</i>-geranylconiferyl alcohol, a metabolite of <i style="">Fagara rhetza</i>
Authors: Mahajan, Rajesh P
Patil, Shamkant L
Mali, Raghao S
Keywords: Methyl ferulates
Wittig reaction
Issue Date: Jan-2006
Publisher: CSIR
Series/Report no.: <b>Int.Cl.<sup>7</sup> C 07 C</b>
Abstract: A convenient two step stereoselective synthesis of (<i style="">E</i>)-methyl <i style="">O</i>-alkylferulate 5a-c is described from vanillin <b>1</b>. Reaction of vanillin <b>1 </b> with allyl-, prenyl- or geranyl- bromide <b> 2a-c </b> has afforded alkyl ethers <b>3a-c </b> which on reaction with phosphorane <b>4 </b>, under microwave irradiation, gives (<i style="">E</i>)-methyl <i style="">O</i>-alkylferulates <b>5a-c </b> in high yield. In an alternative approach vanillin <b>1 </b> on reaction with phosphorane <b>4 </b> provides (<i style="">E</i>)-methyl ferulate <b>6 </b> which on reaction with the corresponding bromides <b>2a-c </b> gives (<i style="">E</i>)-methyl <i style="">O</i>-alkylferulates <b>5a-c </b>.
Description: 328-331
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.45B(01) [January 2006]

Files in This Item:
File Description SizeFormat 
IJCB 45B(1) 328-331.pdf93.21 kBAdobe PDFView/Open

Items in NOPR are protected by copyright, with all rights reserved, unless otherwise indicated.