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

HRID 1295241Notes

Reaction equation

HRID 1295241 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13](OCC)=[O:14])[C:10]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Li+].[Al+3].[H-].[H-].[H-].O>O1CCCC1>[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][OH:14])[C:10]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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

To a solution of ethyl 1-benzyl-3-benzyloxy-1H-pyrazole-4-carboxylate (58.90 g) in tetrahydrofuran (500 ml) was added aluminum lithium hydride (6.64 g) at 0° C. and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixture and the precipitate was filtered off. The filtrate was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and 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 a fraction eluted with ethyl acetate. The crystals were recrystallized from ethyl acetate-hexane. melting point: 79–80° C.

Workup

  1. filtrationthe precipitate was filtered off
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-87e67d0ffe254f3c8fcc31771853d080
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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