Dimethylformamide → ethyl (E)-3-(3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)propenoate

HRID 1295277ノート

反応式

HRID 1295277 の反応式
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([CH:14]=O)[N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O:25][CH2:26][CH2:27]P(OCC)(OCC)=O)(=[O:24])[CH3:23].CN(C)C=O.[H-].[Na+]>O>[CH2:1]([O:8][C:9]1[CH:13]=[C:12](/[CH:14]=[CH:23]/[C:22]([O:25][CH2:26][CH3:27])=[O:24])[N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 124696282-(Diethoxyphosphoryl)ethyl acetateHCID 22930766HCID 22930766、化合物

生成物 1

HCID 86591672ethyl (E)-3-(3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)propenoate収率 94%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of 3-benzyloxy-1-phenyl-1H-pyrazole-5-carbaldehyde (6.24 g), diethylphosphonoethyl acetate (5.55 g) and N,N-dimethylformamide (50 ml) was added sodium hydride (60% in oil, 960 mg) at 0° C. and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with dilute hydrochloric acid and then saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl (E)-3-(3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)propenoate (7.33 g, yield 94%) was obtained as a pale-yellow oil from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with dilute hydrochloric acid
  3. dry with materialsaturated brine, dried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-cb1cbae60cc7460dab25e56964225bee
出典データセット
uspto-grants-2007_07
特許番号
US07241785B2

反応ノート

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