Hexane → [3-Methyl-1-(pyridin-2-yl)-1H-pyrazol-4-yl]methanol

HRID 1294191Notes

Reaction equation

HRID 1294191 reaction equation
[CH3:1][C:2]1[C:6]([C:7](OCC)=[O:8])=[CH:5][N:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+].CCCCCC>O1CCCC1>[CH3:1][C:2]1[C:6]([CH2:7][OH:8])=[CH:5][N:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:3]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 62649Sodium sulfate decahydrateHCID 9877977ethyl 3-methyl-1-(2-pyridyl)-1H-pyrazole-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 23076503[3-Methyl-1-(pyridin-2-yl)-1H-pyrazol-4-yl]methanolYield 92.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-methyl-1-(2-pyridyl)-1H-pyrazole-4-carboxylate (15.00 g) in tetrahydrofuran (150 mL) was added lithium aluminum hydride (1.93 g) at 0° C., and the mixture was stirred at room temperature for 1 hr. Sodium sulfate 10 hydrate (21.03 g) and hexane (100 mL) were added to the reaction mixture, and the mixture was stirred at room temperature for 1 hr. The precipitate was removed by filtration and the filtrate was concentrated. The obtained crystals were collected by filtration to give [3-methyl-1-(2-pyridyl)-1H-pyrazol-4-yl]methanol (11.38 g). The crystals were recrystallized from acetone-hexane. melting point: 116-117° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. customThe precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. filtrationThe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-2f2c036c73ee4a1984c52435a441672d
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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