Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 23076344 | HCID 23076344 | — |
| Reactant | HCID 178519806 | HCID 178519806 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 86605816 | HCID 86605816 | 78.4% |
Reaction Steps
To a mixture of methyl 5-(chloromethyl)-2-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzoate (1.16 g), 3-hydroxy-1-phenyl-1H-pyrazole-4-carbaldehyde (0.50 g) and N,N-dimethylformamide (30 mL) was added sodium hydride (60% in oil, 0.12 g) at room temperature, and the mixture was stirred at 90° C. for 2 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give methyl 5-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}-2-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzoate as colorless crystals (1.07 g, yield 77%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 173-174° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07368578B2 |
|---|
| Source dataset | uspto-grants-2008_05 |
|---|
| ORD ID | ord-10457ddefbe649dba910f214b60dc285 |
|---|
| Source note | uspto-grants-2008_05 |
|---|