Dimethylacetamide → 1-(5-Chloropyridin-2-yl)ethan-1-one

HRID 1437268

반응식

HRID 1437268 반응식
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1.CN(C)[C:16](=[O:18])[CH3:17]>CCCCCC.C(OCC)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:16](=[O:18])[CH3:17])=[N:8][CH:9]=1

참가 물질

6

반응물 3

HCID 31374DimethylacetamideHCID 8170982-Bromo-5-chloropyridineHCID 178418339Butyllithium

생성물 1

HCID 101541661-(5-Chloropyridin-2-yl)ethan-1-one

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

Under cooling at −78° C., 1.56M n-butyllithium in hexane (27 mL) was added dropwise to 2-bromo-5-chloropyridine (6.8 g) in diethyl ether (45 mL), and then N,N-dimethylacetamide (5 mL) was added dropwise thereto, followed by stirring for 30 minutes. The reaction mixture was partitioned by use of saturated aqueous ammonium chloride and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, and the residue was purified through silica gel column chromatography (hexane-ethyl acetate), to thereby give 1-(5-chloro-2-pyridyl)ethanone as a solid (3.26 g, 59%).

후처리

  1. customThe reaction mixture was partitioned by use of saturated aqueous ammonium chloride and ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  3. filtrationfollowed by filtration
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified through silica gel column chromatography (hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-54878bc4476e4bd69c7dbfe10a028619
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622471B2

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