Sodium Hydroxide → (1-benzyl-5-phenyl-1H-pyrazol-3-yl)methanol

HRID 1397457Notes

Reaction equation

HRID 1397457 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:17][C:16]([C:25](OCC)=[O:26])=[N:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[CH2:7]([N:14]1[C:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:17][C:16]([CH2:25][OH:26])=[N:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 67325415HCID 67325415, compound

Product 1

HCID 67324379(1-benzyl-5-phenyl-1H-pyrazol-3-yl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., LAH (1.8 mL, 3.7 mmol, 2M in THF) was added to ethyl 1-benzyl-5-phenyl-1H-pyrazole-3-carboxylate (560 mg, 1.8 mmol) in THF (18 mL). The reaction was stirred for 10 min and then warmed to room temperature for 1 h. Minimal water was slowly added to the reaction followed by 1 mL of 5 M sodium hydroxide. The reaction was stirred for 30 min, sodium sulfate was added, and the solids were removed by filtration. The filtrate was concentrated under reduced pressure to yield crude (1-benzyl-5-phenyl-1H-pyrazol-3-yl)methanol, which was carried through without further purification. MS (ESI) m/z: Calculated for C17H16N2O: 264.13. found: 265.1 (M+H)+.

Workup

  1. stirringThe reaction was stirred for 30 min
  2. customthe solids were removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5563138d49d7435f8e491e7390ad0119
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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