Water → [1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazol-4-yl]methanol

HRID 349903Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:37]=[CH:36][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([C:25](OCC)=[O:26])[C:22]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:21]2)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>O1CCCC1>[CH2:7]([O:14][C:15]1[CH:37]=[CH:36][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([CH2:25][OH:26])[C:22]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[N:21]2)=[CH:17][CH:16]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminium hydride (884 mg) was added to a solution of ethyl 1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazole-4-carboxylate (9.61 g) in tetrahydrofuran (50 ml) at 0° C., and the mixture was stirred at 0° C. for one hour. After adding water, the reaction mixture was stirred at room temperature for one hour. After 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 crystals obtained were collected by filtration to yield [1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazol-4-yl]methanol (23.10 g, yield: 97%). This was recrystallized from ethyl acetate-hexane. Melting point: 88–89° C.

Workup

stirringthe reaction mixture was stirred at room temperature for one hour
customAfter the precipitate was removed by filtration
extractionthe filtrate was extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
dry with materialdried (MgSO4)
concentrationconcentrated
customThe crystals obtained
filtrationwere collected by filtration

Sources & evidence

ORD record: ord-c289402912204c95b7358d80f6cd0f62
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179823B1

Reaction notes

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