Dimethyl Sulfoxide → HCID 19738046, compound

HRID 2255397Notes

Reaction equation

HRID 2255397 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 19738046HCID 19738046, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-eda1257f3b7c44ac8914353154a60b15
Source dataset
uspto-grants-1993_08
Patent number
US05240925

Reaction notes

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