Dimethylformamide → ethyl (E)-3-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)propenoate

HRID 1295261ノート

反応式

HRID 1295261 の反応式
[CH2:1]([O:8][C:9]1[C:13]([CH:14]=O)=[CH:12][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[C:13](/[CH:14]=[CH:23]/[C:22]([O:25][CH2:26][CH3:27])=[O:24])=[CH:12][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 229307603-benzyloxy-1-phenyl-1H-pyrazole-4-carbaldehyde

生成物 1

HCID 86591670ethyl (E)-3-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)propenoate収率 85%

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-4-carbaldehyde (3.00 g), diethylphosphonoethyl acetate (2.67 g) and N,N-dimethylformamide (50 ml) was added sodium hydride (60% in oil, 0.52 g) at 0° C. and the mixture was stirred at room temperature for 15 hrs. 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 saturated brine, dried (MgSO4) and concentrated. The obtained crystals were collected by filtration to give ethyl (E)-3-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)propenoate (3.18 g, yield 85%), which was then recrystallized from ethyl acetate-hexane. melting point: 105–106° C.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with dilute hydrochloric acid and saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. filtrationThe obtained crystals were collected by filtration

出典と根拠

ORDレコード
ord-7b9c200b46324f22be5ad943d1103ac3
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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