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

HRID 1295247Notes

Reaction equation

HRID 1295247 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([C:14](OCC)=[O:15])=[CH:12][N:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[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]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 22930780ethyl 3-benzyloxy-1-phenyl-1H-pyrazole-4-carboxylate

Product 1

HCID 22930694(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)methanolYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-benzyloxy-1-phenyl-1H-pyrazole-4-carboxylate (8.06 g) in tetrahydrofuran (100 ml) was added aluminum lithium hydride (0.95 g) at 0° C. and the mixture was stirred at room temperature for 1 hr. Sodium sulfate 10 hydrate (8.06 g) was added to the reaction mixture and the mixture was stirred at room temperature for 1 hr. The precipitate was filtered off and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and (3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)methanol (5.91 g, yield 84%) was obtained as colorless crystals from a fraction eluted with ethyl acetate. The crystals were recrystallized from ethyl acetate-hexane. melting point: 93–94° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. filtrationThe precipitate was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bf8058436a50416eae55c999fc2bce79
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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