Ethyl bromoacetate → HCID 70410920, compound

Participants

Reaction Steps

A solution of 14.9 g (35.2 mmol) of [[[2-(2-methoxyethoxy)ethoxy]carbonyl]methylene]triphenylphosphorane (preparation see paragraph (c)) in 100 ml of toluene was treated with 4.48 g (17.6 mmol) of (E)-1-bromo-4-(3-methoxyphenyl)-3-buten-2-one (preparation see paragraph d)). The reaction mixture was stirred at reflux for 2 hours and then filtered. After the addition of 1.63 ml (17.6 mmol) of ethyl bromoacetate, the filtrate was again stirred at reflux for 2 hours. The separated solid was filtered off. The filtrate was concentrated and purified by flash chromatography on 500 g of silica gel (elution agent ether/hexane 10:1). Crystallization of the purified product from methylene chloride/ether/hexane yielded 2-(2-methoxyethoxy)ethyl (E,E)-6-(3-methoxyphenyl)-4-oxo-2,5-hexadienoate of melting point 59°-60°.

Provenance & Evidence