Reaktionsgleichung
[Na].[CH3:2][CH:3]([C:6](=O)[CH3:7])[CH:4]=O.[C:9]([CH2:11][C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[O:13])#[N:10].N1CCCCC1.C(O)(=O)C>CN(C)C=O>[CH:15]([N:14]1[C:6]([CH3:7])=[C:3]([CH3:4])[CH:2]=[C:11]([C:9]#[N:10])[C:12]1=[O:13])([CH3:17])[CH3:16]Komponenten
Reaktionsbedingungen
- Temperatur
- 135 °C
Versuchsvorschrift
To a stirred solution of 2-methyl-3-oxobutanal sodium salt (2.73 g, 22.4 mmol, prepared according to Paine, John B et al., J. Heterocycl. Chem., 1987, 24, 351), 2-cyano-N-isopropylacetamide (2.17 g, 17.2 mmol, prepared according to Wuerthner, Frank et al., J. Amer, Chem. Soc., 2002, 32, 9431) in N,N-dimethylformamide (17.2 mL) were added piperidine (292 mg, 3.43 mmol) and acetic acid (1.34 g, 22.4 mmol) successively at room temperature, and the mixture was stirred at 135° C. for 7 h. After cooling, the mixture was quenched with water (100 mL), extracted with dichloromethane (50 mL×4). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (v/v=2/1˜1/1) to give 840 mg (26%) of the title compound as an orange colored solid.
Aufarbeitung
- temperatureAfter cooling
- customthe mixture was quenched with water (100 mL)
- extractionextracted with dichloromethane (50 mL×4)
- dry with materialThe combined organic layers were dried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (v/v=2/1˜1/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-a4071861ccbc4390bfd0536b42284a79
- Quelldatensatz
- uspto-grants-2013_01
- Patentnummer
- US08362038B2
Verknüpfte Notizen
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