Microwave-assisted rapid synthesis of methyl 2,4,5-trimethoxyphenylpropionate, a metabolite of Cordia alliodora.
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).
Sinha
A K
AK
Natural Plant Products Division, Institute of Himalayan Bioresource Technology, Palampur (H.P.)-176061, India. aksinha8@rediffmail.com
Joshi
B P
BP
Sharma
A
A
Kumar
J K
JK
Kaul
V K
VK
D000447:Aldehydes / Q000737:chemistry; D031213:Cordia / Q000737:chemistry*; D008314:Malonates; D008872:Microwaves; D010666:Phenylpropionates / Q000138:chemical synthesis*
D000447:Aldehydes; D008314:Malonates; D010666:Phenylpropionates; C478866:methyl 3-(2,4,5-trimethoxyphenyl)propionate; C030290:malonic acid; C449741:asaronaldehyde