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

HRID 37588

반응식

HRID 37588 반응식
[F:1][C:2]1([F:11])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[O:3]1.CN(CCN(C)C)C.C([Li])CCC.[CH2:25]([O:27][C:28](=[O:36])[C:29](=[CH:32]OCC)[C:30]#[N:31])[CH3:26]>C1(C)C=CC=CC=1.O>[CH2:25]([O:27][C:28](=[O:36])/[C:29](/[C:30]#[N:31])=[CH:32]/[C:10]1[C:4]2[O:3][C:2]([F:1])([F:11])[O:6][C:5]=2[CH:7]=[CH:8][CH:9]=1)[CH3:26]

참가 물질

7

반응물 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 741032,2-Difluoro-1,3-benzodioxoleHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 178418339Butyllithium

생성물 1

HCID 67735358(E)-2-cyano-3-(2,2-difluoro-1,3-benzodioxol-4-yl)-2-propenoic acid ethyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

실험 절차

40.0 g (253 mmol) of 2,2-difluoro-1,3-benzodioxole in 29.5 g (254 mmol) of TMEDA and 35 ml of toluene are metallated analogously to Example 2c) at from -15° to -10° C. with 106.2 g (307 mmol) of n-butyllithium solution (18.5% in toluene). 52.1 g (308 mmol) of ethoxymethylenecyanoacetic acid ethyl ester in 115 ml of toluene are added to the reaction mixture at from -15° to -10° C. over a period of 2 hours. The resulting suspension is poured, after 20 minutes at +10° C., into 350 ml of water, the aqueous phase is separated off and the organic phase is concentrated by evaporation in a vacuum rotary evaporator to yield the desired product.

후처리

  1. customat from -15° to -10° C.
  2. customthe aqueous phase is separated off
  3. concentrationthe organic phase is concentrated by evaporation in a vacuum rotary evaporator

출처 및 근거

ORD 기록
ord-7d92c00c0e584bdda70e88162aee2abd
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420301

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