Reaktionsgleichung
[OH:1][N:2]=[C:3]([CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:4]#[N:5].[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(N(CC)CC)C.O>O1CCCC1>[CH3:16][S:17]([O:1][N:2]=[C:3]([CH:6]=[CH:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)[C:4]#[N:5])(=[O:19])=[O:18]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
2-hydroxyimino-4-(4-methoxy-phenyl)-but-3-enenitrile (1.8 g; 9 mmol) is dissolved in 15 ml of anhydrous tetrahydrofuran, and cooled to 0° C. Methanesulfonyl chloride (0.93 ml, 0.012 mol) is added at once, followed by triethylamine (2 ml, 0.015 mol) dropwise over 20 min, keeping the temperature of the mixture below 5° C. The mixture is then stirred at 2° C. for 1 h 15 min, and poured into 200 ml of iced water. The suspension is extracted with ethyl acetate, the organic extract is washed neutral with water, then with brine, and dried over magnesium sulfate. Rotary evaporation of the solvent and recrystallization from 80 ml of ethanol yields 2-methylsulfonyloxyimino-4-(4-methoxy-phenyl)-but-3-enenitrile (1.02 g; 41%) as light yellow hair-like crystals, mp 147-152° C. (dec). 1H-NMR reveals the presence of only one isomer.
Aufarbeitung
- customthe temperature of the mixture below 5° C
- extractionThe suspension is extracted with ethyl acetate
- extractionthe organic extract
- washis washed neutral with water
- dry with materialwith brine, and dried over magnesium sulfate
- customRotary evaporation of the solvent and recrystallization from 80 ml of ethanol
Quellen und Nachweise
- ORD-Eintrag
- ord-212d808d04a24f93b79c9b42fc64dcf5
- Quelldatensatz
- uspto-grants-2004_03
- Patentnummer
- US06703182B1
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