Formaldehyde → Ethyl 2,2-difluoro-3-hydroxypropanoate
Reaktionsgleichung
[CH2:1]=[O:2].[F:3][C:4]([F:11])(Br)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl-].[NH4+]>O1CCCC1.[Zn]>[F:3][C:4]([F:11])([CH2:1][OH:2])[C:5]([O:7][CH2:8][CH3:9])=[O:6]Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of paraformaldehyde (4.5 g, 50 mmol), ethyl difluorobromoacetate (10.2 g, 50 mmol) and activated zinc dust (3.3 g, 40 mmol) in anhydrous tetrahydrofuran was heated under reflux for 0.5 h. Then the mixture was treated with a saturated aqueous solution of ammonium chloride and extracted with diethyl ether. After usual work-up the desired compound ethyl 2,2-difluoro-3-hydroxypropionate was obtained by flash chromatography on silica gel (ethyl acetate:hexane; 25:75) (4.1 g, 53%).
Aufarbeitung
- temperaturewas heated
- temperatureunder reflux for 0.5 h
- extractionextracted with diethyl ether
Quellen und Nachweise
- ORD-Eintrag
- ord-07cd20d9a5744d628778aeaa05aa92ac
- Quelldatensatz
- uspto-grants-1995_05
- Patentnummer
- US05416076
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