Sodium sulfate decahydrate → (3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)methanol

HRID 2221611Notes

Reaction equation

HRID 2221611 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14](OC)=[O:15])[N:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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[CH:13]=[C:12]([CH2:14][OH:15])[N:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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 22930789methyl 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylate

Product 1

HCID 22930692(3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)methanolYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylate (14.53 g) and tetrahydrofuran (300 mL) was gradually added lithium aluminum hydride (1.79 g) at 0° C. and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was gradually added sodium sulfate decahydrate (15.20 g) at 0° C., and the mixture was stirred at room temperature for 30 min. The insoluble material was removed by filtration, and the mother liquid was concentrated. The residue was subjected to silica gel column chromatography to give (3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)methanol (11.65 g, yield 88%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:2, v/v). The crystals were recrystallized from ethyl acetate-hexane. melting point: 87-88° C.

Workup

  1. customat 0° C.
  2. customat 0° C.
  3. stirringthe mixture was stirred at room temperature for 30 min
  4. customThe insoluble material was removed by filtration
  5. concentrationthe mother liquid was concentrated

Sources & evidence

ORD record
ord-2d32d0d785c84d6e835ca449bbdaceee
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…