Sodium hydride → 2-(3-chlorophenyl)-2-phenylOxirane

HRID 365453

Reaktionsgleichung

Reaktionsgleichung von HRID 365453
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[Cl:9][C:10]1[CH:11]=[C:12]([CH:21]=[CH:22][CH:23]=1)[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14]>CS(C)=O>[Cl:9][C:10]1[CH:11]=[C:12]([C:13]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:4][O:14]2)[CH:21]=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 660983-ChlorobenzophenoneHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)

Produkt 1

HCID 125490722-(3-chlorophenyl)-2-phenylOxirane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A 250 mL-round bottom flask was charged with NaH (60% dispersion in mineral oil) (1.92 g, 0.048 mol), washed with petroleum ether, then treated with dry DMSO (40 mL) under N2. To this reaction mixture was added trimethylsulfoxonium iodide (10.56 g, 0.048 mol) through a solid addition funnel over 15 min. After stirring for 0.5 hr, a solution of 3-chlorobenzophenone (8.66 g, 0.04 mol) in DMSO (15 mL) was added dropwise, and the mixture was heated at 55° C. for 2 hr. The mixture was added to ice-water, extracted with ether (3×100 mL), the organics combined, dried (MgSO4), filtered, and concentrated to give the title compound.

Aufarbeitung

  1. washwashed with petroleum ether
  2. additiontreated with dry DMSO (40 mL) under N2
  3. additionthrough a solid addition funnel over 15 min
  4. extractionextracted with ether (3×100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3e5c83623dbe4e958dfd751ade8d27a0
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127366

Verknüpfte Notizen

Wird geladen…