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

HRID 349923

Reaction equation

HRID 349923 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[C:12]([C:13](OCC)=[O:14])=[CH:11][N:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:9]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].CCCCCC>O1CCCC1>[CH3:7][C:8]1[C:12]([CH2:13][OH:14])=[CH:11][N:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:9]=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

Lithium aluminium hydride (1.93 g) was added to a solution of ethyl 3-methyl-1-(2-pyridyl)-1H-pyrazole-4-carboxylate (15.00 g) in tetrahydrofuran (150 ml) at 0° C., and the mixture was stirred at room temperature for one hour. Sodium sulfate decahydrate (21.03 g) and hexane (100 ml) were added to the reaction mixture, and the mixture was stirred at room temperature for one hour. After the precipitate was removed by filtration, the filtrate was concentrated. The crystals obtained were collected by filtration to yield [3-methyl-1-(2-pyridyl)-1H-pyrazol-4-yl]methanol (11.38 g). This was recrystallized from acetone-hexane. Melting point: 116–117° C.

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. customAfter the precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customThe crystals obtained
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-f629b2eadfef435bb5d41732fed7d2f2
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Linked notes

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