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

HRID 30681

反応式

HRID 30681 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1bd55c209f4d461382b28eb878c6df98
出典データセット
uspto-grants-2008_09
特許番号
US07423159B2

関連ノート

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