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

HRID 1295248ノート

反応式

HRID 1295248 の反応式
[CH2:1]([N:8]1[CH:12]=[C:11]([CH:13]=O)[C:10]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O:26][CH2:27][CH2:28]P(OCC)(OCC)=O)(=[O:25])[CH3:24].CN(C)C=O.[H-]>O>[CH2:1]([N:8]1[CH:12]=[C:11](/[CH:13]=[CH:24]/[C:23]([O:26][CH2:27][CH3:28])=[O:25])[C:10]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:9]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 166653HydrideHCID 124696282-(Diethoxyphosphoryl)ethyl acetateHCID 229307681-benzyl-3-(benzyloxy)-1H-pyrazole-4-carbaldehyde

生成物 1

HCID 69421683ethyl(E)-3-(1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)propenoate収率 91%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of 1-benzyl-3-benzyloxy-1H-pyrazole-4-carbaldehyde (12.90 g), diethylphosphonoethyl acetate (9.60 ml) and N,N-dimethylformamide (200 ml) was added hydride (60% in oil, 1.94 g) at 0° C., and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dilute hydrochloric acid, washed successively with saturated brine, dried (MgSO4) and concentrated. The obtained crystals were collected by filtration to give ethyl (E)-3-(1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)propenoate (14.50 g, yield 91%). The crystals were recrystallized from ethyl acetate-hexane. melting point: 88–89° C.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed successively with 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-8bc7b9e224904d77bc089c0d72c48e33
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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