Triethyl phosphonoacetate → ethyl(E)-3-(1-benzyl-5-phenyl-1H-pyrazol-4-yl)propenoate

HRID 349921ノート

反応式

HRID 349921 の反応式
[H-].[Na+].[CH2:3]([N:10]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:13]([CH:21]=O)[CH:12]=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OP([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])(OCC)=O)C>CN(C)C=O>[CH2:3]([N:10]1[C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:13](/[CH:21]=[CH:31]/[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:12]=[N:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 230247651-benzyl-5-phenyl-1H-pyrazole-4-carbaldehyde

生成物 1

HCID 69421709ethyl(E)-3-(1-benzyl-5-phenyl-1H-pyrazol-4-yl)propenoate収率 71%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60%, oily, 1.28 g) was added to a mixture of 1-benzyl-5-phenyl-1H-pyrazole-4-carbaldehyde (7.00 g), ethyl diethylphosphonoacetate (6.59 g), and N,N-dimethylformamide (100 ml) at 0° C., and the mixture was stirred at room temperature for 2.5 days. The reaction mixture was poured into ice water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and ethyl(E)-3-(1-benzyl-5-phenyl-1H-pyrazol-4-yl)propenoate (6.30 g, yield: 71%) was obtained as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 62–63° C.

後処理

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-ba61161a4e8d4b528c322224fe9f2260
出典データセット
uspto-grants-2007_02
特許番号
US07179823B1

反応ノート

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