HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Ethanol → 4-Chloro-3-hydroxybutyric acid ethyl ester, (3R)-
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Ethanol | HCID 702 | — |
| Edukt | Tetrahydrofuran | HCID 8028 | — |
| Edukt | (-)-Epichlorohydrin | HCID 2734062 | — |
| Edukt | HCID 178418416 | HCID 178418416 | — |
| Katalysator | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Produkt | 4-Chloro-3-hydroxybutyric acid ethyl ester, (3R)- | HCID 2734445 | 83% |
Reaktionsschritte
In a 50 mL-volumetric autoclave were added deaerated ethanol (10 mL) and THF (10 mL), and thereto were added 4-dimethylaminopyridine (61 mg, 0.5 mmol) and (R)-epichlorohydrin (1.9 g, 20 mmol, >99% ee). Then to the mixture was added crystalline dicobaltoctacarbonyl complex (171 mg, 0.5 mmol). After covering the autoclave with a cap, carbon monoxide (2 MPa) was introduced therein and the mixture was reacted at 40° C. for 16 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give (R)-4-chloro-3-hydroxybutanoic acid ethyl ester (2.8 g, 83%, >99% ee) as a colorless oil.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07256305B2 |
| Quelldatensatz | uspto-grants-2007_08 |
| ORD ID | ord-45a96af85e0c447998bd29199eafaee4 |
| Quellennotiz | uspto-grants-2007_08 |