Ethanol → {4-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]phenyl}methanol

HRID 507970Notes

Reaction equation

HRID 507970 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]([CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19](OC)=[O:20])=[CH:17][CH:16]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)C.[Cl-].[NH4+]>O1CCCC1>[C:1]([C:5]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:19][OH:20])=[CH:23][CH:24]=2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 23157342methyl 4-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]benzoate

Product 1

HCID 23157370{4-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]phenyl}methanolYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]benzoate (1.72 g, 5.24 mmol) in tetrahydrofuran (35 mL) was added lithium aluminum hydride (0.25 g, 5.3 mmol) at 0° C., and the mixture was stirred at room temperature for 30 min. Ethanol (10 mL) and saturated aqueous ammonium chloride solution (1.0 mL) were added to the reaction mixture, and the precipitated solid was filtered off. The filtrate was concentrated and the residue was purified by silica gel column chromatography (50% ethyl acetate/hexane) to give the title compound (1.28 g, yield 81%) as colorless crystals.

Workup

  1. filtrationthe precipitated solid was filtered off
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by silica gel column chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6ac7d862e21d4a048e0065cf4b372b43
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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