Sodium Sulfate → (5-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-methanol

HRID 220478Notes

Reaction equation

HRID 220478 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[CH:13]=[N:14][N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[C:16]=1[CH3:17])=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:17][C:16]1[N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:14]=[CH:13][C:12]=1[CH2:10][OH:9]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 222675745-methyl-1-pyridin-2-yl-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 66438330(5-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-methanolYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add lithium aluminum hydride (0.225 g, 5.92 mmol) to tetrahydrofuran (15 mL) at 0° C. then slowly add 5-methyl-1-pyridin-2-yl-1H-pyrazole-4-carboxylic acid ethyl ester (0.685 g, 2.96 mmol) in tetrahydrofuran (5 mL) dropwise. Warm the mixture to room temperature and stir for 2 hr. then cool the solution to 0° C. Add saturated aqueous sodium sulfate (0.5 mL), warm to room temperature then stir for 2 hr. Filter off the solid materials then dry the solution (sodium sulfate), filter and concentrate to give (5-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-methanol as a white solid (0.501 g, 89%).

Workup

  1. temperaturethen cool the solution to 0° C
  2. stirringthen stir for 2 hr
  3. filtrationFilter off the solid materials
  4. dry with materialthen dry the solution (sodium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-4d41f922366e417d877497454476d7e8
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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