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

HRID 507963Notes

Reaction equation

HRID 507963 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10](OCC)=[O:11])[N:7]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][O:23][CH2:24][O:25][CH3:26])=[CH:18][CH:17]=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]([CH2:10][OH:11])[N:7]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][O:23][CH2:24][O:25][CH3:26])=[CH:20][CH:21]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 23157202ethyl 3-tert-butyl-1-{4-[(methoxymethoxy)methyl]benzyl}-1H-pyrazole-5-carboxylate

Product 1

HCID 23157325(3-tert-butyl-1-{4-[(methoxymethoxy)methyl]benzyl}-1H-pyrazol-5-yl)methanolYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-tert-butyl-1-{4-[(methoxymethoxy)methyl]benzyl}-1H-pyrazole-5-carboxylate (1.95 g, 5.41 mmol) in tetrahydrofuran (20 mL) was added lithium aluminum hydride (0.26 g, 5.5 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 (1.45 g, yield 84%) as a colorless oil.

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-b2c32c8786cd4fb6b0d8ec37c2e1dcb7
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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