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

HRID 572224ノート

反応式

HRID 572224 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7271880bafdd456dafd33f1ba8247240
出典データセット
uspto-grants-2015_05
特許番号
US09029386B2

反応ノート

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