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

HRID 572224Notes

Reaction equation

HRID 572224 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

HCID 86641862(R)-2-chloro-6-(1-(3-nitrophenyl)ethoxy)pyrazineYield 89.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7271880bafdd456dafd33f1ba8247240
Source dataset
uspto-grants-2015_05
Patent number
US09029386B2

Reaction notes

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