Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate | HCID 9925856 | — |
| Reactant | HCID 140584041 | HCID 140584041 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 88531363 | HCID 88531363 | 71% |
Reaction Steps
To a solution of (E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate (1.0 g, 3.5 mmol) and (E)-1-(4-hydroxy-2,5-dimethylphenyl)ethanone propyloxime (0.6 g, 4.2 mmol) obtained in Step 5 in 20 mL of acetonitrile (CH3CN) was added cesium carbonate (1.7 g, 5.2 mmol), followed by stirring at room temperature for 3 hours. The reaction solvent was removed by concentration in a vacuum. The residue was stirred in water (20 mL) and the aqueous layer was extracted twice with 20 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in a vacuum to remove the solvent. The concentrate was purified through silica gel chromatography to afford (E)-methyl 2-(2-((2,5-dimethyl-4-((E)-1-(propoxyimino)ethyl)phenoxy)methyl)phenyl)-3-methoxyacrylate as a white oil (0.88 g, yield 71%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08772290B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-7aba1687b45240fe90c04a135de878d8 |
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| Source note | uspto-grants-2014_07 |
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