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

HRID 1295261노트

반응식

HRID 1295261 반응식
[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

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 124696282-(Diethoxyphosphoryl)ethyl acetateHCID 229307603-benzyloxy-1-phenyl-1H-pyrazole-4-carbaldehyde

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7b9c200b46324f22be5ad943d1103ac3
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241785B2

반응 노트

불러오는 중…