Ethanol → Ethyl 3-[(2,6-dinitrophenyl)amino]-2,2-difluoropropanoate
Reaktionsgleichung
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[NH:13][CH2:14][C:15]([F:20])([F:19])[C:16]([OH:18])=[O:17])([O-:3])=[O:2].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+].[CH2:31](O)[CH3:32]>>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[NH:13][CH2:14][C:15]([F:19])([F:20])[C:16]([O:18][CH2:31][CH3:32])=[O:17])([O-:3])=[O:2]Komponenten
5
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
To a solution of 3-[(2,6-dinitrophenyl)amino]-2,2-difluoropropanoic acid (3.52 g, 12.09 mmol) in ethanol (30.0 mL) was added sulfuric acid (4 mL) at 0° C. The reaction mixture was stirred at 100° C. for 1 hr. After cooling, the reaction mixture was neutralized with aqueous saturated sodium hydrogen carbonate and the solvent was removed. The residue was extracted with ethyl acetate (×3). The combined organic layer was washed with brine (×1), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-20% ethyl acetate/n-hexane gradient mixture to give the title compound as a yellow oil (2.94 g, 9.210 mmol, 76%).
Aufarbeitung
- temperatureAfter cooling
- customthe solvent was removed
- extractionThe residue was extracted with ethyl acetate (×3)
- washThe combined organic layer was washed with brine (×1)
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography
- washeluting with a 0-20% ethyl acetate/n-hexane gradient mixture
Quellen und Nachweise
- ORD-Eintrag
- ord-25cff3b28e904d30aa17fbc29505dc05
- Quelldatensatz
- uspto-grants-2014_12
- Patentnummer
- US08901141B2
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