Hydrochloric Acid → Ethyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate
Reaktionsgleichung
[H-].[Na+].[Cl:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1.CN(C)C=O.Br[CH2:22][CH2:23]Cl.Cl>CCOC(C)=O>[Cl:3][C:4]1[N:9]=[CH:8][C:7]([C:10]2([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:23][CH2:22]2)=[CH:6][CH:5]=1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 35 °C
Versuchsvorschrift
Sodium hydride (60% in mineral oil, 0.60 g, 15 mmol) was added to a solution of ethyl (6-chloropyridin-3-yl)acetate (1.0 g, 0.0050 mol) in N,N-dimethylformamide (10 mL, 0.1 mol) at rt under an atmosphere of nitrogen. After 30 minutes, 1-bromo-2-chloro-ethane (0.84 mL, 0.010 mol) was added to the mixture at 0° C. The reaction mixture was stirred at 35° C. for 4 hours and then at room temperature overnight. The mixture was poured into a mixture of ice-water (50 ml) and EtOAc (50 ml) and the resulting mixture was acidified (to pH 2) by slow addition of 6 N HCl. The layers were separated and the organic layer was washed successively with water and brine, dried over MgSO4 and concentrated. The residue was chromatographed by combiflash (ethyl acetate in hexanes: 80%, on silica gel) to afford the desired product. LC/MS: 226.0 and 228.0 (M+H+).
Aufarbeitung
- customat room temperature
- customovernight
- customThe layers were separated
- washthe organic layer was washed successively with water and brine
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe residue was chromatographed by combiflash (ethyl acetate in hexanes: 80%, on silica gel)
Quellen und Nachweise
- ORD-Eintrag
- ord-926bb072b96d4e1cb6f33cc5ac04ff81
- Quelldatensatz
- uspto-grants-2010_08
- Patentnummer
- US07776874B2
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