Dimethylformamide → HCID 23025025, compound

HRID 350205Notes

Reaction equation

HRID 350205 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.[CH2:12]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:28](=[O:31])([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:12]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:4]2[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]([O:1][CH2:12][C:13]3[CH:14]=[CH:15][C:16]([O:31][CH2:28][C:21]4[CH:20]=[CH:27][CH:26]=[CH:23][CH:22]=4)=[CH:17][CH:18]=3)=[N:3]2)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 700424-Benzyloxybenzyl chlorideHCID 178469940HCID 178469940, compound

Product 1

HCID 23025025HCID 23025025, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 3-hydroxy-1H-pyrazol-4-carboxylate (10.30 g), 4-benzyloxybenzyl chloride (18.60 g), potassium carbonate (16.60 g), and N,N-dimethylformamide (200 ml) was stirred at 100° C. overnight. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid, then, with saturated aqueous sodium chloride solution, and dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 1-(4-benzyloxybenzyl)-3-(4-benzyloxybenzyloxy)-1H-pyrazol-4-carboxylate (11.90 g, yield: 54%) was obtained as colorless crystals from the fraction eluted with ethyl acetate. This was recrystallized from ethyl acetate-hexane. Melting point: 124–125° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with dilute hydrochloric acid
  3. dry with materialwith saturated aqueous sodium chloride solution, and dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bff40e7ad7334c67b74938314bac3df2
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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