Potassium Carbonate → 2-(2-(2-fluoro-5-nitrophenoxy)ethoxy)tetrahydro-2H-pyran
Reaktionsgleichung
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].Br[CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1Komponenten
7
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
A mixture of 2-fluoro-5-nitrophenol (4 g, 25 mmol), 2-(2-bromoethoxy)tetrahydro-2H-pyran (4.4 mL, 28 mmol) and potassium carbonate (4.2 g 30 mmol) in DMF (50 mL) was stirred at 50° C. for 16 h. The reaction was cooled to room temperature, diluted with EtOAc and H2O. The aqueous layer was separated and extracted with EtOAc. The combined organic extracts were washed with H2O (5×'s to remove DMF) and brine and dried over sodium sulfate. The resulting residue was purified by column chromatography ISCO Rf (40 g column) eluting with a gradient of 100% hexanes—1:1 hexanes:EtOAc to provide 2-(2-(2-fluoro-5-nitrophenoxy)ethoxy)tetrahydro-2H-pyran XXII.
Aufarbeitung
- temperatureThe reaction was cooled to room temperature
- customThe aqueous layer was separated
- extractionextracted with EtOAc
- washThe combined organic extracts were washed with H2O (5×'
- customto remove DMF) and brine
- dry with materialdried over sodium sulfate
- customThe resulting residue was purified by column chromatography ISCO Rf (40 g column)
- washeluting with a gradient of 100% hexanes—1:1 hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-d8f317bf6f3e45b78281483b5923c0b9
- Quelldatensatz
- uspto-grants-2016_03
- Patentnummer
- US09290505B2
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