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Acetonitrile → ethyl 1-ethyl-4-fluoro-1H-pyrazole-5-carboxylate

HRID 244660
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HRID 244660 반응식
[CH2:1]([N:3]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=[N:4]1)[CH3:2].[B-](F)(F)(F)[F:14].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.C(#N)C>C(O)(=O)C>[CH2:1]([N:3]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:14])[CH:5]=[N:4]1)[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 2724933Selectfluor2회HCID 23005846Ethyl 1-ethyl-1H-pyrazole-5-carboxylate

생성물 1

HCID 58356399ethyl 1-ethyl-4-fluoro-1H-pyrazole-5-carboxylate

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

A microwave vial was charged with ethyl 1-ethyl-1H-pyrazole-5-carboxylate (0.2 g) and Selectfluor™ (0.548 g) followed by acetonitrile (3 ml) and acetic acid (0.5 ml). The mixture was heated at 100° C. under microwave irradiation for 120 min. Selectfluor™ (0.548 g) was added and the mixture was heated was heated at 100° C. under microwave irradiation for 60 min. The solvent was removed in vacuo and the residue was partitioned between DCM (15 ml) and water (15 ml) and separated by hydrophobic frit. The aqueous layer was washed with dichloromethane (2×5 ml) and the combined organic layers concentrated in vacuo. Purification by chromatography on silica gel (20 g silica cartridge) eluting with a gradient of 0-50% DCM in cyclohexane over 20 min gave the title compound (67 mg) as a colourless oil.

후처리

  1. temperaturethe mixture was heated
  2. temperaturewas heated at 100° C. under microwave irradiation for 60 min
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between DCM (15 ml) and water (15 ml)
  5. customseparated by hydrophobic frit
  6. washThe aqueous layer was washed with dichloromethane (2×5 ml)
  7. concentrationthe combined organic layers concentrated in vacuo
  8. customPurification by chromatography on silica gel (20 g silica cartridge)
  9. washeluting with a gradient of 0-50% DCM in cyclohexane over 20 min

출처 및 근거

ORD 기록
ord-53283dd5af544aa19a3d3f9adc3942ad
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658635B2

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