Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Trimethylboroxine | HCID 574072 | — |
| Reactant | HCID 57815175 | HCID 57815175 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 57815358 | HCID 57815358 | 74.2% |
Reaction Steps
To a solution of 0.50 g of (5-methoxy-4-(((trifluoromethyl)sulfonyl)oxy)pyridin-2-yl)methyl acetate in 5 mL of dioxane, 0.63 g of potassium carbonate, 0.21 mL of trimethylboroxin and 0.18 g of tetrakis(triphenylphosphine)palladium(0) were added, and the mixture was stirred at 70 to 90° C. for 3 hours under a nitrogen atmosphere. The mixture was heated under reflux while further stirring for 3 hours, after cooling to room temperature, water and ethyl acetate were added to the reaction mixture, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate, the organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with hexane:ethyl acetate=80:20 to 50:50 to obtain 0.22 g of (5-methoxy-4-methylpyridin-2-yl)methyl acetate as a yellow oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08367831B2 |
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| Source dataset | uspto-grants-2013_02 |
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| ORD ID | ord-b0cbd9d442eb4faf93e38e7e9e9f08f1 |
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| Source note | uspto-grants-2013_02 |
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