Reaktionsgleichung
CO[CH:3]=[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:5]#[N:6].C[O-].[Na+].[C:16]([O:20][CH3:21])(=[O:19])[CH2:17][SH:18]>>[NH2:6][C:5]1[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:3][S:18][C:17]=1[C:16]([O:20][CH3:21])=[O:19]Komponenten
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
3-Methoxy-2-phenylacrylonitrile (17.9 g, 112.5 mmol) was dissolved in NaOMe (5 M in MeOH, 31.5 ml, 157.5 mmol), and then methyl thioglycolate (16 ml, 180.0 mmol) was added thereto. The mixture was heated with stirring at 65° C. for 24 hr. After the completion of the reaction was confirmed by thin layer chromatography (TLC), the reaction mixture was cooled to room temperature and filtered through Celite. The filtrate was washed with distilled water and extracted with dichloromethane. The organic layer was dried over anhydrous MgSO4 and filtered. The filtrate was distilled under reduced pressure, and the concentrate was purified by silica gel column chromatography (EtOAc:Hex=1:5) to give 5.1 g (21.9 mmol, 26% yield in three steps) of the title compound.
Aufarbeitung
- temperatureThe mixture was heated
- temperaturethe reaction mixture was cooled to room temperature
- filtrationfiltered through Celite
- washThe filtrate was washed with distilled water
- extractionextracted with dichloromethane
- dry with materialThe organic layer was dried over anhydrous MgSO4
- filtrationfiltered
- distillationThe filtrate was distilled under reduced pressure
- customthe concentrate was purified by silica gel column chromatography (EtOAc:Hex=1:5)
Quellen und Nachweise
- ORD-Eintrag
- ord-7b527c2a61394df98de362b0cf7a98af
- Quelldatensatz
- uspto-grants-2016_02
- Patentnummer
- US09260448B2
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