Sodium sulfate decahydrate → [3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazol-4-yl]methanol

HRID 2221697Notes

Reaction equation

HRID 2221697 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:9]([C:10](OCC)=[O:11])=[CH:8][N:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[N:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:9]([CH2:10][OH:11])=[CH:8][N:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[N:6]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 23076555ethyl 3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 69217086[3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazol-4-yl]methanolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazole-4-carboxylate (2.39 g) in tetrahydrofuran (60 mL) was added lithium aluminum hydride (0.323 g) at 0° C. and the mixture was stirred at room temperature for 16 hrs. Sodium sulfate decahydrate (2.78 g) was added to the reaction mixture and the mixture was stirred at room temperature for 1 hr. After removing the precipitate by filtration, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:1-4:1, v/v) to give [3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazol-4-yl]methanol as a pale-yellow oil (1.84 g, yield 90%).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. customAfter removing the precipitate
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated
  5. washeluted with ethyl acetate-hexane (1:1-4:1

Sources & evidence

ORD record
ord-7f518e1bf19445459449b27335b872a5
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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