Ethanol → Ethyl 4-(1H-pyrazol-1-YL)benzoate

HRID 563288

反応式

HRID 563288 の反応式
[N:1]1([C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.S(=O)(=O)(O)O.[CH3:20][CH2:21]O>>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:10]([O:12][CH2:20][CH3:21])=[O:11])=[CH:13][CH:14]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

参加物

4

反応物 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 7365274-(1H-pyrazol-1-yl)benzoic acid

生成物 1

HCID 973146Ethyl 4-(1H-pyrazol-1-YL)benzoate

実験手順

To a solution of 4-(1H-pyrazol-1-yl)benzoic acid (CAS 160209-00-0, 678 mg, 3.60 mmol) in absolute EtOH (10 mL) was added sulfuric acid (0.1 mL) at room temperature. The reaction mixture was heated to reflux and stirred for 71 h, then concentrated under reduced pressure. The residue was partitioned between sat. aq. NaHCO3 (60 mL) and EtOAc (50 mL). The aqueous layer was extracted with EtOAc (50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to provide the title compound as an off white solid (711 mg, 91%): 1H NMR (400 MHz, CDCl3, δ in ppm) 8.14 (d, J=8.6 Hz, 2H), 8.01 (d, J=2.5 Hz, 1H), 7.78 (d, J=8.8 Hz, 2H), 7.78-7.75 (m, 1H), 6.51 (t, J=1.8 Hz, 1H), 4.39 (q, J=7.2 Hz, 2H), 1.41 (t, J=7.0 Hz, 3H).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between sat. aq. NaHCO3 (60 mL) and EtOAc (50 mL)
  5. extractionThe aqueous layer was extracted with EtOAc (50 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-fc7de25a49c64dbfa364813fdabc80d3
出典データセット
uspto-grants-2011_11
特許番号
US08067448B2

関連ノート

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