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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1614005Erstellt: 24. Oktober 2026

Toluene → (E)-2-cyano-3-(2,2-difluoro-1,3-benzodioxol-4-yl)-2-propenoic acid ethyl ester

https://huagongshe.com/de/reaction/1614005

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTolueneHCID 1140—
EduktN,N,N',N'-TetramethylethylenediamineHCID 8037—
Edukt2,2-Difluoro-1,3-benzodioxoleHCID 74103—
EduktMethyl 2-cyano-3-ethoxy-2-propenoateHCID 101455—
EduktButyllithiumHCID 178418339—
LösungsmittelWaterHCID 962—
Produkt(E)-2-cyano-3-(2,2-difluoro-1,3-benzodioxol-4-yl)-2-propenoic acid ethyl esterHCID 67735358—

Reaktionsschritte

53.3 g (337 mmol) of 2,2-difluoro-1,3-benzodioxole in 46 ml of toluene are metallated according to Example 2d), at from -15° to -10° C., with 137.8 g (409 mmol) of n-butyllitium solution (19.0% in toluene) in the presence of 39.3 g (339 mmol) of TMEDA. 69.1 g (409 mmol) of ethoxymethylenecyanoacetic acid methyl ester in 150 ml of toluene are metered in at from -15° to -10° C. over a period of 21/2 hours. The reaction mixture is added at +10° C. to 450 ml of water, the phases are separated and the organic phase is concentrated by evaporation in a vacuum rotary evaporator to yield the title compound.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS05194628
Quelldatensatzuspto-grants-1993_03
ORD IDord-f68d2296da7c4f7894dd521f6eeb9ef1
Quellennotizuspto-grants-1993_03