Sodium sulfate decahydrate → (1-ethyl-1H-pyrazol-4-yl)methanol

HRID 2221660Notes

Reaction equation

HRID 2221660 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]1[CH:13]=[C:12]([C:14](OCC)=[O:15])[CH:11]=[N:10]1)[CH3:8].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:7]([N:9]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[N:10]1)[CH3:8]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 17862887HCID 17862887, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 4711794(1-ethyl-1H-pyrazol-4-yl)methanolYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (7.19 g) was suspended in tetrahydrofuran (400 mL). To the obtained mixture were added a solution (100 mL) of ethyl 1-ethyl-1H-pyrazole-4-carboxylate (29.00 g) in tetrahydrofuran on an ice bath with stirring. After stirring the reaction mixture at room temperature for 1.5 hrs, sodium sulfate decahydrate (80 g) was added by small portions on an ice bath with stirring, and the mixture was further stirred at room temperature for 16 hrs. The solid was filtered, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give (1-ethyl-1H-pyrazol-4-yl)methanol as a colorless oil (16.85 g, yield 78%) from a fraction eluted with ethyl acetate-methanol (1:0 to 49:1, v/v).

Workup

  1. stirringAfter stirring the reaction mixture at room temperature for 1.5 hrs
  2. stirringwith stirring
  3. stirringthe mixture was further stirred at room temperature for 16 hrs
  4. filtrationThe solid was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0c204cfa04594a2b8504ffe83a411fad
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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