Dimethylformamide → ethyl 1-(4-phenoxybenzyl)-3-(4-phenoxybenzyloxy)-1H-pyrazole-4-carboxylate

HRID 350305

Reaction equation

[OH:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1.[O:12]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:27](=[O:30])([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:12]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:4]2[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]([O:1][CH2:23][C:22]3[CH:21]=[CH:20][C:19]([O:30][C:27]4[CH:15]=[CH:14][CH:13]=[CH:18][CH:17]=4)=[CH:26][CH:25]=3)=[N:3]2)=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of ethyl 3-hydroxy-1H-pyrazole-4-carboxylate (8.95 g), 4-phenoxybenzyl chloride (25.35 g), potassium carbonate (31.88 g), and N,N-dimethylformamide (200 ml) was stirred at 90° C. for 8 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed successively with dilute hydrochloric acid and aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 1-(4-phenoxybenzyl)-3-(4-phenoxybenzyloxy)-1H-pyrazole-4-carboxylate (22.71 g, yield: 76%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

Workup

extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed successively with dilute hydrochloric acid and aqueous sodium chloride solution
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-8f7f8ede6a8d4eaca18ad63c178f6634
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179823B1

Linked notes

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