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

HRID 349921노트

반응식

HRID 349921 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ba61161a4e8d4b528c322224fe9f2260
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179823B1

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