Sodium hydride → HCID 64906466, Verbindung

HRID 518778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 518778
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.Br[CH2:12][C:13](OC)([O:16]C)[CH2:14]Br.[H-].[Na+]>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:9]#[N:10])[CH2:14][C:13](=[O:16])[CH2:12]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 36023(3-Bromophenyl)acetonitrileHCID 27341961,3-Dibromo-2,2-dimethoxypropane

Produkt 1

HCID 64906466HCID 64906466, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To 3-bromophenylacetonitrile (7.55 g, 38.5 mmol) and 1,3-dibromo-2,2-dimethyoxypropane (10.09 g, 38.5 mmol) in dry DMSO (100 ml) was added in two portions sodium hydride (3.23 g of 60% dispersion in oil, 81 mmol) while the mixture was cooled in a water bath. The mixture was stirred at RT for 10 minutes, and heated at 60° C. in an oil bath for 6 hours. The reaction was diluted with water and extracted with EtOAc. The organic layer was separated, washed with water and the solvent removed. The residual red oil was eluted through a short pad of silica, eluent 10% EtOAc/Hexane. The resulting ketal was dissolved in acetone (100 ml) and 1N aqueous HCl (10 ml) and heated at reflux for 6 hours under a nitrogen atmosphere. The solvent was removed and the residue was neutralized by treatment with aqueous NaHCO3 and extracted with EtOAc. The solvent was removed and the residue was chromatographed (SiO2, eluent 10% EtOAc in hexane) to give a yellow oil which solidified on drying under vacuum.

Aufarbeitung

  1. temperaturewas cooled in a water bath
  2. temperatureheated at 60° C. in an oil bath for 6 hours
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with water
  6. customthe solvent removed
  7. washThe residual red oil was eluted through a short pad of silica, eluent 10% EtOAc/Hexane
  8. dissolutionThe resulting ketal was dissolved in acetone (100 ml)
  9. temperature1N aqueous HCl (10 ml) and heated
  10. temperatureat reflux for 6 hours under a nitrogen atmosphere
  11. customThe solvent was removed
  12. extractionextracted with EtOAc
  13. customThe solvent was removed
  14. customthe residue was chromatographed (SiO2, eluent 10% EtOAc in hexane)
  15. customto give a yellow oil which
  16. customon drying under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2d631801a82e481abd00099077767d2a
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115127B2

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