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Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.45B [2006] >
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
microwave
Wittig reaction |
| Issue Date: | Jan-2006 |
| Publisher: | CSIR |
| IPC Code: | Int.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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