Potassium Hydroxide → (1-benzyl-1H-pyrazol-4-yl)methanol

HRID 2261297Notes

Reaction equation

HRID 2261297 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH:18]=[C:17]([C:19](OC)=[O:20])[CH:16]=[N:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[K+]>O1CCCC1>[CH2:7]([N:14]1[CH:18]=[C:17]([CH2:19][OH:20])[CH:16]=[N:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydrideHCID 45073393Methyl 1-benzyl-1H-pyrazole-4-carboxylate

Product 1

HCID 16769828(1-benzyl-1H-pyrazol-4-yl)methanolYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen atmosphere, 1.44 g of lithium aluminum hydride was added to 100 ml of tetrahydrofuran, and a solution of 7.39 g of methyl 1-benzyl-1H-pyrazole-4-carboxylate in 50 ml of tetrahydrofuran was added dropwise at 0° C. over 30 minutes. Thereafter, the mixture was stirred at room temperature for 5 hours. The reaction mixture was cooled to 0° C., and 15 ml of a 1 mol/L aqueous potassium hydroxide solution was added dropwise. Precipitates were filtered, washed with tetrahydrofuran and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 6.32 g of (1-benzyl-1H-pyrazol-4-yl)methanol.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customPrecipitates
  3. filtrationwere filtered
  4. washwashed with tetrahydrofuran
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9df0a5f6958b4546af460d0b06b562dd
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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