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

HRID 563288

반응식

HRID 563288 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fc7de25a49c64dbfa364813fdabc80d3
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067448B2

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