Reaktionsgleichung
[CH3:1][O:2][C:3]([C@@H:5]1[C@@H:7]([CH:8]=O)[C:6]1([CH3:11])[CH3:10])=[O:4].[C:12](#[N:17])[CH2:13][CH:14]=[CH:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]([C@@H:5]1[C@@H:7](/[CH:8]=[C:13](\[C:12]#[N:17])/[CH:14]=[CH:15]/[CH3:16])[C:6]1([CH3:11])[CH3:10])=[O:4]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Methyl-(1R)-trans-3-formyl-2,2-dimethylcyclopropane carboxylate (2.53 g, 16.2 mmol), 3-pentenonitrile (1.90 g, 23.5 mmol) and anhydrous potassium carbonate (3.22 g, 23.3 mmol) were added to 30 mL of N,N-dimethylformamide and the mixture was stirred at room temperature for 24 hours. The reaction solution was added to 100 mL of ice water and the solution was extracted twice with each 100 mL of ethyl acetate. The obtained ethyl acetate layers were combined, washed once with 50 mL of saturated brine and then dried over magnesium sulfate. After concentration under reduced pressure condition, the residue was subjected to silica gel column chromatography to obtain 0.94 g of methyl-(1R)-trans-3-[(1Z,3E)-2-cyano-1,3-pentadienyl]-2,2-dimethylcyclopropane carboxylate represented by the following formula:
Aufarbeitung
- extractionthe solution was extracted twice with each 100 mL of ethyl acetate
- washwashed once with 50 mL of saturated brine
- dry with materialdried over magnesium sulfate
- concentrationAfter concentration under reduced pressure condition
Quellen und Nachweise
- ORD-Eintrag
- ord-b1889586d72540b6b701374b678ff34b
- Quelldatensatz
- uspto-grants-2013_07
- Patentnummer
- US08487115B2
Verknüpfte Notizen
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