Ethyl 4-(1H-pyrazol-1-YL)benzoate → (4-(1H-Pyrazol-1-yl)phenyl)methanol

HRID 629359

Reaction equation

HRID 629359 reaction equation
[N:1]1([C:6]2[CH:16]=[CH:15][C:9]([C:10](OCC)=[O:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[BH4-].[Na+].[Cl-].[Ca+2].[Cl-]>C1COCC1.Cl>[N:1]1([C:6]2[CH:16]=[CH:15][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

6

Reactant 3

HCID 973146Ethyl 4-(1H-pyrazol-1-YL)benzoateHCID 4311764Sodium borohydrideHCID 5284359Calcium Chloride

Product 1

HCID 2776480(4-(1H-Pyrazol-1-yl)phenyl)methanolYield 83.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(1H-pyrazol-1-yl)benzoate (73.7 g) in THF (500 mL) were added sodium borohydride (19.5 g) and calcium chloride (56.8 g) under ice-cooling, and the mixture was stirred at room temperature for 16 hr, and then heated with reflux for 2 days. The reaction mixture was diluted with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate (×4). The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was washed with tert-butyl methyl ether to give the title compound (49.6 g).

Workup

  1. temperaturecooling
  2. temperatureheated
  3. temperaturewith reflux for 2 days
  4. extractionthe mixture was extracted with ethyl acetate (×4)
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. washthe residue was washed with tert-butyl methyl ether

Sources & evidence

ORD record
ord-5166db553cfa4411a7c1264e42643cf0
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Linked notes

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