Dimethylformamide → HCID 23076460, compound

HRID 2221852Notes

Reaction equation

HRID 2221852 reaction equation
Cl[CH2:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[O:12][C:13]=2[CH3:14])=[C:5]([O:22][CH2:23][CH3:24])[CH:4]=1.[OH:25][C:26]1[C:30]([CH:31]=[O:32])=[CH:29][N:28]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:27]=1.CN(C)C=O.[H-].[Na+]>O>[CH2:23]([O:22][C:5]1[CH:4]=[C:3]([CH:21]=[CH:20][C:6]=1[O:7][CH2:8][C:9]1[N:10]=[C:11]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[O:12][C:13]=1[CH3:14])[CH2:2][O:25][C:26]1[C:30]([CH:31]=[O:32])=[CH:29][N:28]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:27]=1)[CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 230764394-(4-Chloromethyl-2-ethoxyphenoxy)methyl-5-methyl-2-(2-furyl)-1,3-oxazoleHCID 178519806HCID 178519806, compound

Product 1

HCID 23076460HCID 23076460, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-(4-chloromethyl-2-ethoxyphenoxy)methyl-5-methyl-2-(2-furyl)-1,3-oxazole (0.56 g), 3-hydroxy-1-phenyl-1H-pyrazole-4-carbaldehyde (0.25 g) and N,N-dimethylformamide (20 mL) was added sodium hydride (60% in oil, 0.06 g) at room temperature. After stirring the reaction mixture at room temperature for 30 min, the mixture was stirred at 90° C. for 2 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 3-[(3-ethoxy-4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzyl)oxy]-1-phenyl-1H-pyrazole-4-carbaldehyde as colorless crystals (0.56 g, yield 86%) from a fraction eluted with tetrahydrofuran-hexane (1:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 149-150° C.

Workup

  1. stirringthe mixture was stirred at 90° C. for 2 hrs
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fe773797f3664c74a63c68a05e5ff3fc
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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