Ethylene Glycol → 5-(1,3-Dioxolan-2-YL)-2-fluoropyridine

HRID 561011

Reaktionsgleichung

Reaktionsgleichung von HRID 561011
[F:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1.[CH2:10](O)[CH2:11][OH:12].C1COCC1>C(Cl)(Cl)Cl.C(O)(C)C.O.O.[Cu](Cl)Cl>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[N:7][CH:6]=1

Komponenten

6

Edukt 3

HCID 174Ethylene GlycolHCID 8028TetrahydrofuranHCID 164142462-Fluoro-5-formylpyridine

Produkt 1

HCID 601557925-(1,3-Dioxolan-2-YL)-2-fluoropyridineAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 61482Cupric chloride dihydrateKatalysatorHCID 21906603Chloroform isopropyl alcoholLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a pressure vessel, combine 6-fluoro-pyridine-3-carbaldehyde (4 g, 32 mmol), ethylene glycol (3 g, 48 mmol), copper (II) chloride di-hydrate (0.56 g, 3.2 mmol) and THF (10 mL). Heat the mixture at 100° C. for 1 hour. Dilute the mixture with chloroform-isopropanol (3:1, 100 mL). Wash the organic phase with saturated aqueous sodium chloride and water. Dry the organic layer over sodium sulfate. Concentrate the solution in vacuo to brown oil. Purify by column chromatography (20% ethyl acetate in hexane) to afford the title compound (2.1 g, 39%) as a pale yellow oil. MS (ES) m/z 170 [M+1]+.

Aufarbeitung

  1. customIn a pressure vessel, combine
  2. washWash the organic phase with saturated aqueous sodium chloride and water
  3. dry with materialDry the organic layer over sodium sulfate
  4. concentrationConcentrate the solution in vacuo to brown oil
  5. customPurify by column chromatography (20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f668c9cefe1e479794ff2c53df520d50
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063212B2

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