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

HRID 244660
ノート
印刷プレビュー

反応式

HRID 244660 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 2724933Selectfluor2 回HCID 23005846Ethyl 1-ethyl-1H-pyrazole-5-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-53283dd5af544aa19a3d3f9adc3942ad
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08658635B2

反応ノート

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