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

HRID 1198751

반응식

HRID 1198751 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.C([Li])[CH2:13][CH2:14][CH3:15].C[N:18](CCN(C)C)C.C[O:26][C:27](=[O:35])C(=COCC)C#N.[C:36]1([CH3:42])C=CC=CC=1>O>[CH2:36]([O:35][C:27](=[O:26])/[C:14](/[C:13]#[N:18])=[CH:15]/[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)[CH3:42]

참가 물질

7

반응물 5

HCID 1140Toluene2회HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 741032,2-Difluoro-1,3-benzodioxoleHCID 101455Methyl 2-cyano-3-ethoxy-2-propenoateHCID 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 1

HCID 962Water용매

실험 절차

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-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.

후처리

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

출처 및 근거

ORD 기록
ord-f6780c078b0b4c99b1572d119cf0274a
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05281718

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