Dimethylformamide → (E)-Ethyl 3-(1-methyl-1H-pyrazol-4-yl)acrylate

HRID 30681

반응식

HRID 30681 반응식
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=O)[CH:4]=[N:3]1.[H-].[Na+].C(OP([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])(OCC)=O)C.CN(C)C=O>O>[CH3:1][N:2]1[CH:6]=[C:5](/[CH:7]=[CH:19]/[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:4]=[N:3]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 5731171-Methyl-1H-pyrazole-4-carbaldehyde

생성물 1

HCID 68356132(E)-Ethyl 3-(1-methyl-1H-pyrazol-4-yl)acrylate수율 64.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 1-methyl-1H-pyrazole-4-carbaldehyde (2.59 g), sodium hydride (60% in oil, 1.13 g), ethyl diethylphosphonoacetate (5.8 g) and N,N-dimethylformamide (50 ml) was stirred at room temperature for 2 hrs. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give ethyl (2E)-3-(1-methyl-1H-pyrazol-4-yl)acrylate (2.72 g, 64%) as crystals from a fraction eluted with hexane-ethyl acetate (1:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 43-44° C.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1bd55c209f4d461382b28eb878c6df98
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423159B2

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