Glyoxal → 1-(4-hydroxy-1-phenyl-1H-pyrazol-3-yl)ethanone

HRID 1880328

반응식

HRID 1880328 반응식
[C:1]1([NH:7][N:8]=[CH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13]([CH:15]=O)=[O:14]>C(O)(=O)C>[OH:12][C:10]1[C:9]([C:13](=[O:14])[CH3:15])=[N:8][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:11]=1

참가 물질

4

반응물 2

HCID 7860GlyoxalHCID 2204342-Oxopropanal phenylhydrazone

생성물 1

HCID 134133951-(4-hydroxy-1-phenyl-1H-pyrazol-3-yl)ethanone수율 43.4%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To 2-oxopropanal phenylhydrazone (5.00 g, 30.8 mmol) in acetic acid (60 mL) was added a 40% aqueous solution of glyoxal (5.9 g, 4.6 mL, 30.8 mmol) and the mixture was heated at reflux for 45 minutes. The acetic acid was removed under reduced pressure. The resultant mixture was diluted with ethyl acetate (100 mL), washed with NaHCO3 and sat. aq. NaCl. Solids were removed by filtration, the filtrate was dried over Na2SO4, filtered and concentrated. The crude material was purified by CombiFlash (180 g column, 0-20 EtOAc/heptane gradient) to afford 1-(4-hydroxy-1-phenyl-1H-pyrazol-3-yl)ethanone as a yellow solid (2.70 g, 43%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 45 minutes
  3. customThe acetic acid was removed under reduced pressure
  4. additionThe resultant mixture was diluted with ethyl acetate (100 mL)
  5. washwashed with NaHCO3 and sat. aq. NaCl
  6. customSolids were removed by filtration
  7. dry with materialthe filtrate was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material was purified by CombiFlash (180 g column, 0-20 EtOAc/heptane gradient)

출처 및 근거

ORD 기록
ord-4685bdcabab04375a1f86305a6097dba
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318762B2

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