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

HRID 629359

Reaktionsgleichung

Reaktionsgleichung von HRID 629359
[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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 2776480(4-(1H-Pyrazol-1-yl)phenyl)methanolAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5166db553cfa4411a7c1264e42643cf0
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315458B2

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