Dimethyl Sulfoxide → 2-(2-Methoxyphenyl)-3-(tetrahydropyran-2-yl)propionitrile

HRID 2255397노트

반응식

HRID 2255397 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].Br[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1.CS(C)=O.[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)[C:10]#[N:11]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 81496(2-Methoxyphenyl)acetonitrileHCID 1419172-(Bromomethyl)tetrahydro-2H-pyran

생성물 1

HCID 197380462-(2-Methoxyphenyl)-3-(tetrahydropyran-2-yl)propionitrile수율 82%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a flask was added 20 g. (0.1346 mole) of (2-methoxyphenyl)acetonitrile, 25 g. (0.1346 mole) of 2-(bromomethyl)tetrahydro-2H-pyran, and 200 ml. of DMSO. The mixture was stirred for five minutes at room temperature and to the resultant solution was added 22 g. (0.2692 mole) of 50% aqueous sodium hydroxide over 30 minutes with the reaction temperature being allowed to exotherm to 60° C. The reaction was stirred an additional two hours, then cooled, water added and the organic material extracted with ether. The combined ether extracts were then washed with water, dried, filtered, and the ether distilled. The organic residue wss fractionally distilled to obtain 27 g. (82% yield) of the 2-(2-methoxyphenyl)-3-(tetrahydropyran-2-yl)propionitrile boiling 145°-160° C. at 5 mm of Hg.

후처리

  1. additionTo a flask was added 20 g
  2. additionwas added 22 g
  3. customto exotherm to 60° C
  4. temperaturecooled
  5. extractionthe organic material extracted with ether
  6. washThe combined ether extracts were then washed with water
  7. customdried
  8. filtrationfiltered
  9. distillationthe ether distilled
  10. distillationThe organic residue wss fractionally distilled
  11. customto obtain 27 g

출처 및 근거

ORD 기록
ord-eda1257f3b7c44ac8914353154a60b15
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05240925

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