Water → (1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)methanol

HRID 349937Notes

Reaction equation

HRID 349937 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH:18]=[C:17]([C:19](OCC)=[O:20])[C:16]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>O1CCCC1>[CH2:7]([N:14]1[CH:18]=[C:17]([CH2:19][OH:20])[C:16]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22930773ethyl 1-benzyl-3-benzyloxy-1H-pyrazole-4-carboxylate

Product 1

HCID 22930765(1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)methanolYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (6.64 g) was added to a solution of ethyl 1-benzyl-3-benzyloxy-1H-pyrazole-4-carboxylate (58.90 g) in tetrahydrofuran (500 ml) at 0° C., and the mixture was stirred at room temperature for 30 minutes. After the reaction mixture was poured into water and the precipitate was removed by filtration, the filtrate was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and (1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)methanol (45.30 g, yield: 88%) was obtained as colorless crystals from the fraction eluted with ethyl acetate. This was recrystallized from ethyl acetate-hexane. Melting point: 79–80° C.

Workup

  1. customthe precipitate was removed by filtration
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8c03df8a45a346a8b9671e12d5d331f1
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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