Reaktion #546612

Reaktionsgleichung

n-butyllithium

diethylphosphonoacetic acid

phenoxyacetaldehyde

formaldehyde

diethylamine hydrochloride salt

→

2-Formylvinyl phenyl ether

5-phenoxy-2,4-pentadienoic acid

Lösungsmittel

tetrahydrofuran

ether

Reaktionsbedingungen

Vorschrift

2-Formylvinyl phenyl ether is prepared by treating phenoxyacetaldehyde with formaldehyde and diethylamine hydrochloride salt. The ether is then reacting with a solution of diethylphosphonoacetic acid and n-butyllithium in anhydrous tetrahydrofuran (THF) to form 5-phenoxy-2,4-pentadienoic acid. 5-Phenoxy-2,4-pentadienal is obtained by first converting the carboxylic acid to a Weinreb amide using oxalyl chloride followed by N,O-dimethylhydroxylamine. Subsequently, reduction of the Weinreb amide with lithium aluminum hydride (LAH) in THF leads to the formation of 5-phenoxy-2,4-pentadienal. The synthesis is summarized in Scheme II.

Quelle