Sodium hydride → (R)-2-chloro-6-(1-(3-nitrophenyl)ethoxy)pyrazine

HRID 1255850Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1255850
[N+:1]([C:4]1[CH:5]=[C:6]([C@H:10]([OH:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Cl:13][C:14]1[CH:19]=[N:18][CH:17]=[C:16](Cl)[N:15]=1.[H-].[Na+].C(=O)([O-])O.[Na+]>O1CCOCC1.C(OCC)(=O)C>[Cl:13][C:14]1[CH:19]=[N:18][CH:17]=[C:16]([O:12][C@@H:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH3:11])[N:15]=1

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 785042,6-DichloropyrazineHCID 516892Sodium BicarbonateHCID 11147933(R)-1-(3-nitrophenyl)ethanol

Produkt 1

HCID 86641862(R)-2-chloro-6-(1-(3-nitrophenyl)ethoxy)pyrazineAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of (R)-1-(3-nitrophenyl)ethanol (167 mg, 1 mmol) and 2,6-dichloropyrazine (164 mg, 1.1 mmol) in dioxane was added sodium hydride (88 mg, 60% oil dispersion, 2.2 mmol) in one portion and the mixture was heated at reflux for 4 hours. After this time the mixture was allowed to cool to room temperature and was poured into saturated aqueous sodium hydrogen carbonate (25 mL) and ethyl acetate (25 mL). The two phases were separated and the aqueous phase was extracted with ethyl acetate (25 mL). The combined organic phases were washed with brine (25 mL), dried (Na2SO4) and concentrated under reduced pressure to give (R)-2-chloro-6-(1-(3-nitrophenyl)ethoxy)pyrazine (250 mg, 89%) as an orange oil.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. customThe two phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (25 mL)
  5. washThe combined organic phases were washed with brine (25 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1db4049eee6e48efaa93c86b44fe124b
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461161B2

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