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

HRID 2221608Notes

Reaction equation

HRID 2221608 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-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([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 lithium aluminum hydride (0.95 g) at 0° C. and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added sodium sulfate decahydrate (8.06 g) and the mixture was stirred at room temperature for 1 hr. After removing the precipitate by filtration, the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give (3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)methanol (5.91 g, yield 84%) 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. customAfter removing the precipitate
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-beea84ec16aa40759749d4d230de88ff
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…