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HRID 37589作成日:2026年10月23日

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

https://huagongshe.com/ja/reaction/37589

反応式

関与物質

役割名称HCID仕込み量
反応物TolueneHCID 1140—
反応物N,N,N',N'-TetramethylethylenediamineHCID 8037—
反応物2,2-Difluoro-1,3-benzodioxoleHCID 74103—
反応物Methyl 2-cyano-3-ethoxy-2-propenoateHCID 101455—
反応物ButyllithiumHCID 178418339—
溶媒WaterHCID 962—
生成物(E)-2-cyano-3-(2,2-difluoro-1,3-benzodioxol-4-yl)-2-propenoic acid ethyl esterHCID 67735358—

反応手順

53.3 g (337 mmol) of 2,2-difluoro-1,3-benzodioxole in 46 ml of toluene are metalated according to Example 2d), at from -15° to -10° C., with 137.8 g (409 mmol) of n-butyllithium 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.

情報源と証拠

DOI10.6084/m9.figshare.5104873.v1
特許番号US05420301
出典データセットuspto-grants-1995_05
ORD IDord-61b678b9b6184ef6bc35ea82c07962dd
出典メモuspto-grants-1995_05