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

HRID 2388489Notes

Reaction equation

HRID 2388489 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-89ad2fd98e5d4016b3b2992c643fa784
Source dataset
uspto-grants-2012_09
Patent number
US08268872B2

Reaction notes

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