HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Water → 4-Methoxy-3-(pyridin-3-yl)benzaldehyde
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Water | HCID 962 | — |
| Edukt | Sodium Carbonate | HCID 10340 | — |
| Edukt | Pyridine-3-boronic acid propane diol | HCID 69587225 | — |
| Katalysator | HCID 178418397 | HCID 178418397 | — |
| Lösungsmittel | Ethanol | HCID 702 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Produkt | 4-Methoxy-3-(pyridin-3-yl)benzaldehyde | HCID 22391521 | 87% |
Reaktionsschritte
Tetrakis(triphenylphosphine)palladium(0) (0.2 g) was added to a solution of 3-bromo-4-methoxybenzldehyde (1.25 g) in toluene (10 ml) and ethanol (10 ml), followed by addition of 2M aqueous sodium carbonate (11 ml). To this mixture was added pyridine-3-boronic acid propane diol (1 g), and the mixture was heated to reflux. After 2 hours, the reaction was added to water (75 ml) and extracted with ethyl acetate (2×75 ml). The combined organic layers were washed with saturated aqueous sodium bicarbonate (100 ml) and brine (100 ml), dried over magnesium sulfate and concentrated. Chromatography (silica, 20-50% ethyl acetate/hexanes) afforded 1.08 g (87%) of 3-(3-pyridyl)-4-methoxybenzaldehyde as a white solid.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US06531502B1 |
| Quelldatensatz | uspto-grants-2003_03 |
| ORD ID | ord-877ab030e4aa47968e538d56a677f0f1 |
| Quellennotiz | uspto-grants-2003_03 |