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

HRID 572224노트

반응식

HRID 572224 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7271880bafdd456dafd33f1ba8247240
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029386B2

반응 노트

불러오는 중…