Diethyl Ether → 1-(Pyridin-2-yl)undecan-1-one

HRID 1587707ノート

反応式

HRID 1587707 の反応式
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)#N.[Cl-].[NH4+].C([O:25]CC)C>>[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)(=[O:25])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

参加物

6

反応物 5

HCID 3283Diethyl Ether2 回HCID 7522Pyridine-2-carbonitrileHCID 81731-BromodecaneHCID 25517Ammonium ChlorideHCID 5462224Magnesium2 回

生成物 1

HCID 197561311-(Pyridin-2-yl)undecan-1-one収率 58.3%

実験手順

To 100 ml of anhydrous ether was added 3.60 g of magnesium for Grignard reaction, and to the mixture was added while stirring 36.5 g of 1-bromodecane. After the magnesium was completely dissolved, a diethyl ether solution of 15.6 g (0.15 mol) of 2-cyanopyridine was added dropwise, and the mixture was refluxed for 7 hours. After cooling, saturated ammonium chloride solution was added, the diethyl ether layer was separated, and the aqueous layer was further extracted with diethyl ether. The ether layers were combined, washed with water, and then dried over anhydrous sodium sulfate. After concentration under a reduced pressure, the residue was purified by separation according to silica gel column chromatography (ethyl acetate:hexane=1:9) to obtain 21.6 g of the desired product (yield 58.3%).

後処理

  1. customfor Grignard reaction
  2. additionto the mixture was added
  3. temperaturethe mixture was refluxed for 7 hours
  4. temperatureAfter cooling
  5. customthe diethyl ether layer was separated
  6. extractionthe aqueous layer was further extracted with diethyl ether
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationAfter concentration under a reduced pressure
  10. customthe residue was purified by separation

出典と根拠

ORDレコード
ord-f9567617c20c4dd59a147ba5286b6cb6
出典データセット
uspto-grants-1993_06
特許番号
US05219847

反応ノート

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