Microwave-assisted rapid synthesis of methyl 2,4,5-trimethoxyphenylpropionate, a metabolite of Cordia alliodora

Nat Prod Res. 2003 Dec;17(6):419-22. doi: 10.1080/14786410310001617686.

Abstract

Microwave assisted condensation of asaronaldehyde (2) with malonic acid in piperidine-AcOH provides 2,4,5-trimethoxycinnamic acid (3) in 87% yield within 4 min, which upon further reduction with PdCl2- HCOOH-aq. NaOH gives 3-(2,4,5-trimethoxy)phenyl propionic acid (4) in 88% yield within 3 min. Esterification of 4 with MeOH-H+ gives methyl 2,4,5-trimethoxyphenylpropionate (1), a metabolite of Cordia alliodora, in 94% yield within 3 min (overall 69% yield).

MeSH terms

  • Aldehydes / chemistry
  • Cordia / chemistry*
  • Malonates
  • Microwaves
  • Phenylpropionates / chemical synthesis*

Substances

  • Aldehydes
  • Malonates
  • Phenylpropionates
  • methyl 3-(2,4,5-trimethoxyphenyl)propionate
  • malonic acid
  • asaronaldehyde