Potassium Hydroxide → (1-Tert-butyl-1h-pyrazol-4-yl)methanol

HRID 2261294Notes

Reaction equation

HRID 2261294 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:11]1[CH:15]=[C:14]([C:16](OC)=[O:17])[CH:13]=[N:12]1)([CH3:10])([CH3:9])[CH3:8].[OH-].[K+]>O1CCCC1>[C:7]([N:11]1[CH:15]=[C:14]([CH2:16][OH:17])[CH:13]=[N:12]1)([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57736385Methyl 1-t-butyl-pyrazole-4-carboxylate

Product 1

HCID 43753535(1-Tert-butyl-1h-pyrazol-4-yl)methanolYield 94.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen atmosphere, 1.25 g of lithium aluminum hydride was suspended in 100 ml of tetrahydrofuran, and a solution of 5.01 g of methyl 1-t-butyl-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 7 hours. The reaction mixture was cooled to 0° C. and 10 ml of a 1 mol/L aqueous potassium hydroxide solution was then added dropwise. Produced precipitates were filtered and washed with tetrahydrofuran. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 4.02 g of (1-t-butyl-1H-pyrazol-4-yl)methanol.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customProduced
  3. customprecipitates
  4. filtrationwere filtered
  5. washwashed with tetrahydrofuran
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-16a20825c4fb4dd7a4f98a85a929b1d4
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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