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IJC-B Vol.45B(01) [January 2006] >

Title: Convenient synthesis of (E)-methyl O-alkylferulates: Formal synthesis of O-geranylconiferyl alcohol, a metabolite of Fagara rhetza
Authors: Mahajan, Rajesh P
Patil, Shamkant L
Mali, Raghao S
Keywords: Methyl ferulates
Wittig reaction
Issue Date: Jan-2006
Publisher: CSIR
IPC CodeInt.Cl.7 C 07 C
Abstract: A convenient two step stereoselective synthesis of (E)-methyl O-alkylferulate 5a-c is described from vanillin 1. Reaction of vanillin 1 with allyl-, prenyl- or geranyl- bromide 2a-c has afforded alkyl ethers 3a-c which on reaction with phosphorane 4 , under microwave irradiation, gives (E)-methyl O-alkylferulates 5a-c in high yield. In an alternative approach vanillin 1 on reaction with phosphorane 4 provides (E)-methyl ferulate 6 which on reaction with the corresponding bromides 2a-c gives (E)-methyl O-alkylferulates 5a-c .
Page(s): 328-331
ISSN: 0975-0983(Online); 0376-4699(Print)
Source:IJC-B Vol.45B(01) [January 2006]

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