Diethyl Ether → 3-tert-Butoxy-5-fluoropyrazine-2-carboxaldehyde

HRID 914845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 914845
[C:1]([O:5][C:6]1[C:7]([CH:13]=[O:14])=[N:8][CH:9]=[C:10](Cl)[N:11]=1)([CH3:4])([CH3:3])[CH3:2].[F-:15].[K+].C1OCCOCCOCCOCCOCCOC1.C(OCC)C>C(#N)C.[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6]1[C:7]([CH:13]=[O:14])=[N:8][CH:9]=[C:10]([F:15])[N:11]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 222482023-Tert-butoxy-5-chloropyrazine-2-carboxaldehyde

Produkt 1

HCID 222482523-tert-Butoxy-5-fluoropyrazine-2-carboxaldehydeAusbeute 3,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2724163Tetraphenylphosphonium BromideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

After dissolving 5.86 g of the crude 3-tert-butoxy-5-chloropyrazine-2-carboxaldehyde in 55 ml of acetonitrile, 4.77 g of potassium fluoride, 1.13 g of tetraphenylphosphonium bromide and 0.71 g of 18-crown-6 were added and the mixture was heated to reflux for 4 hours. Diethyl ether was added to the reaction mixture, the insoluble portion was filtered out, and the filtrate was distilled off under reduced pressure. Ethyl acetate was added to the residue, the insoluble portion was filtered out, and the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: toluene/ethyl acetate) to obtain the title compound (183 mg, 3% yield).

Aufarbeitung

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 4 hours
  4. filtrationthe insoluble portion was filtered out
  5. distillationthe filtrate was distilled off under reduced pressure
  6. additionEthyl acetate was added to the residue
  7. filtrationthe insoluble portion was filtered out
  8. distillationthe filtrate was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (solvent: toluene/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8d8a4b5835b047d2afa733c7d4e8fec0
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265108B2

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