HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → 4-(Pyrazin-2-yl)benzaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Chloropyrazine | HCID 73277 | — |
| Reactant | 4-Formylphenylboronic Acid | HCID 591073 | — |
| Catalyst | (Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1) | HCID 10974057 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-(Pyrazin-2-yl)benzaldehyde | HCID 3853519 | 42.2% |
Reaction Steps
1 M aq. Na2CO3 (20 mL) and ethanol (10 mL) were added to a solution 15 of 2-chloropyrazine (2.30 g, 20.06 mmol), 4-formylphenylboronic acid (3.90 g, 26.01 mmol) and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.60 g, 0.99 mmol) in toluene (40 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.56 g (42%) of 4-pyrazinylbenzaldehyde.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06825172B2 |
| Source dataset | uspto-grants-2004_11 |
| ORD ID | ord-b36cc7482a2f4a4b897b455db28a481c |
| Source note | uspto-grants-2004_11 |