Tetrahydrofuran → Diethyl 2-fluoro-2-phenylmalonate

HRID 2259399

Reaktionsgleichung

Reaktionsgleichung von HRID 2259399
[Na][C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].O1CCCC1.[O-]S(C(F)(F)[F:29])(=O)=O.[O-]S(C(F)(F)F)(=O)=O.F[N+]12CC[N+](F)(CC1)CC2>C(#N)C.C(OCC)C>[F:29][C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 152179651,4-Difluoro-1,4-diazoniabicyclo[2.2.2]octane bistriflateHCID 178472663C13H15NaO4

Produkt 1

HCID 4246642Diethyl 2-fluoro-2-phenylmalonateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A cold (-10° C.) solution of diethyl sodio(phenyl)-malonate in anhydrous tetrahydrofuran [prepared in conventional fashion from sodium hydride (2.5 mmol) and diethyl phenylmalonate (0.5 g, 2.1 mmol) in THF (15 cm3)] was added slowly to a cold (-10° C.) stirred solution of 1,4-difluoro-1,4-diazoniabicyclo[2.2.2]octane bistriflate (0.95 g, 2.12 mmol) in dry acetonitrile (50 cm3) under an atmosphere of nitrogen. The reaction mixture was allowed to warm to room temperature and then diluted with diethyl ether (100 cm3). The mixture was then washed with 0.5M oxalic acid (30 cm3), 10% aqueous potassium hydrogen carbonate (30 cm3), and saturated brine (30 cm3) (in that order), dried (MgSO4), filtered, and the filtrate evaporated under reduced pressure to provide diethyl fluoro(phenyl)-malonate (65% yield) with correct NMR parameters.

Aufarbeitung

  1. washThe mixture was then washed with 0.5M oxalic acid (30 cm3), 10% aqueous potassium hydrogen carbonate (30 cm3), and saturated brine (30 cm3) (in that order)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe filtrate evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bff8bed15d45475c8f836dbd9ebfd39d
Quelldatensatz
uspto-grants-1995_12
Patentnummer
US05473065

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