Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acrylate | HCID 8821 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (6-Bromopyridin-2-yl)methanol | HCID 3517811 | — |
| Catalyst | Tetrabutylammonium Chloride | HCID 70681 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59555434 | HCID 59555434 | — |
Reaction Steps
2-Bromopyridine-6-methanol (2 g) was dissolved in 10 mL of dry DMF, and 1.73 mL of ethyl acrylate, 2.95 g of tetra(n-butyl)ammonium chloride, 1.78 g of sodium bicarbonate and 2 g of Molecular Sieves (Molecular Sieves 3A ( 1/16)) to the above solution, additionally under argon atmosphere 119 mg of palladium(II) acetate was added thereto, and then the mixture was stirred at 80° C. for 5 hours. After being cooled, the insoluble portion was filtrated off, and water was added thereto and then the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (hexane-ethyl acetate=2:1) to give 1.39 g of ethyl 3-(6-hydroxymethylpyridin-2-yl)-trans-acrylate as a light yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07989446B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-c4f8aaa0a50e400ab118046a2e6e611b |
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| Source note | uspto-grants-2011_08 |
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