Hexane → (1-benzyl-5-phenyl-1H-pyrazol-4-yl)methanol

HRID 349919Notes

Reaction equation

HRID 349919 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:17]([C:25](OCC)=[O:26])[CH:16]=[N:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].CCCCCC>O1CCCC1>[CH2:7]([N:14]1[C:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[C:17]([CH2:25][OH:26])[CH:16]=[N:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 23024981ethyl 1-benzyl-5-phenyl-1H-pyrazole-4-carboxylate

Product 1

HCID 23025093(1-benzyl-5-phenyl-1H-pyrazol-4-yl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (2.50 g) was added to a solution of ethyl 1-benzyl-5-phenyl-1H-pyrazole-4-carboxylate (20.2 g) in tetrahydrofuran (300 ml) at 0° C., and the mixture was stirred at room temperature for one hour. Sodium sulfate decahydrate (21.23 g) and hexane (100 ml) were added to the reaction mixture, and the mixture was stirred at room temperature for one hour. After the precipitate was removed by filtration, the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and (1-benzyl-5-phenyl-1H-pyrazol-4-yl)methanol (17.4 g, yield: 100%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio). NMR(CDCl3) δ: 4.46(2H, s), 5.25(2H, s), 6.99–7.04(2H, m), 7.23–7.32(5H, m), 7.41–7.45(3H, m), 7.69(1H, s).

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. customAfter the precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bdaa62306f1a40cd87a47bb73138cd7b
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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