Sodium Cyanide → 3-(1-Adamantyl)propanenitrile

HRID 1925511

Reaktionsgleichung

Reaktionsgleichung von HRID 1925511
CS(O[CH2:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)(=O)=O.[C-:18]#[N:19].[Na+]>CS(C)=O>[C:8]12([CH2:7][CH2:6][C:18]#[N:19])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2

Komponenten

4

Edukt 2

HCID 8929Sodium CyanideHCID 157176822-(1-Adamantyl)ethyl methanesulfonate

Produkt 1

HCID 33669013-(1-Adamantyl)propanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of Intermediate 44 (4.1 g, 16.01 mmol) in dimethyl sulfoxide (18 mL) was slowly added sodium cyanide (0.98 g, 20 mmol). The reaction mixture was stirred at 100° C. for 1.5 hours and at room temperature overnight. The crude was partitioned between ether and water and the organic layer was washed with water. The solvent was removed under reduced pressure and the title compound was obtained as a colourless solid (2.9 g, 98%) and used in the next step without further purification.

Aufarbeitung

  1. customThe crude was partitioned between ether and water
  2. washthe organic layer was washed with water
  3. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7ce11a9a6b6f40e48157489bb09fe894
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178679B2

Verknüpfte Notizen

Wird geladen…