Sodium sulfate decahydrate → (3-benzyloxy-1-methyl-1H-pyrazol-4-yl)methanol

HRID 1295220Notes

Reaction equation

HRID 1295220 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([C:14](OCC)=[O:15])=[CH:12][N:11]([CH3:19])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Li+].[Al+3].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:13]([CH2:14][OH:15])=[CH:12][N:11]([CH3:19])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 22175079Ethyl 3-(benzyloxy)-1-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 22930776(3-benzyloxy-1-methyl-1H-pyrazol-4-yl)methanolYield 158.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-benzyloxy-1-methyl-1H-pyrazole-4-carboxylate (18.00 g) in tetrahydrofuran (200 ml) was added aluminum lithium hydride (2.62 g) at 0° C. and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added sodium sulfate 10 hydrate (22.20 g) and the mixture was stirred at room temperature for 1 hr. The precipitate was removed by filtration and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and (3-benzyloxy-1-methyl-1H-pyrazol-4-yl)methanol (23.90 g, yield 91%) was obtained as a colorless oil from a fraction eluted with ethyl acetate.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. customThe precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-acb7c439626040808634c0dd1e9b8b6d
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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