What is Diethyl ethoxymethylenemalonate?

Identification

Product Name:    Diethyl ethoxymethylenemalonate   

Synonyms:    1,1-DICARBETHOXY-2-ETHOXYETHYLENE;2,2-DICARBETHOXYVINYL ETHYL ETHER;AKOS BBS-00004230;LABOTEST-BB LT02094814;ETHYL A-CARBETHOXY-B-ETHOXYACRYLATE;ETHYL ETHOXYMETHYLENE MALONATE;ETHYL 3-ETHOXY-2-(ETHOXYCARBONYL)ACRYLATE;EMME

CAS:    87-13-8 

MF:    C10H16O5 

MW:    216.23

EINECS:    201-725-7

Structure  

Properties

Melting point     -33°C    

Boiling point     279-283 °C(lit.)   

Density     1.080 g/mL at 20 °C(lit.)   

Vapor pressure     <0.1 hPa    

Refractive index     n20/D 1.463   

Fp     311 °F   

Storage temp.     Refrigerator

Form     Liquid    

Color     Clear colorless to light yellow    

Water Solubility     insoluble

Application

Diethyl ethoxymethylenemalonate is an intermediate in the production of Flumequine, which  can be used as a precursor to synthesize pyrimidinones, thiazolopyrimidines, thiazolopyrimidinones,triazolo [1, 5-a] pyrimidines, pyrimido[2,1-b]benzothiazoles and ethyl 3-amino-5-oxoisoxazolidine-4-carboxylate derivatives.

Purification Methods

Likely impurity is diethyl diethoxymethylene malonate which is difficult to separate from diethyl ethoxymethylene malonate by distillation, and it is necessary to follow the course of the distillation by the change in refractive index instead of boiling point. After a low boiling fraction is collected, there is obtained an intermediate fraction (n 20 1.414—1.458), the size of which depends on the amount of the diethoxymethylene compound. This fraction is fractionated through a 5inch Vigreux column (p 11) at low pressure avoiding interruption in heating. 

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