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

HRID 1437268

反応式

HRID 1437268 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-54878bc4476e4bd69c7dbfe10a028619
出典データセット
uspto-grants-2009_11
特許番号
US07622471B2

関連ノート

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