Reaktion #475446

Reaktionsgleichung

NaHCO3

HCl

2-(4-(dimethylamino)phenyl)-2-(trimethylsilyloxy)acetonitrile

HCl

→

2-(4-(dimethylamino)phenyl)-2-hydroxyacetonitrile

Ausbeute 102.1%

Lösungsmittel

EtOAc

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred for an additional 50 minutes
2. 2
   SonstigeThe layers were separated
3. 3
   Waschenthe organics were washed with saturated aqueous NaHCO3, water and brine
4. 4
   TrocknenThe solution was dried over Na2SO4
5. 5
   Einengenconcentrated in vacuo

Vorschrift

To a solution of 2-(4-(dimethylamino)phenyl)-2-(trimethylsilyloxy)acetonitrile (7.19 g, 28.9 mmol) in THF (35 mL) was added 1 M aqueous HCl (1 mL) and the mixture was stirred for 1 hour. Additional 1 M HCl (1 mL) was then added and the reaction mixture was stirred for an additional 50 minutes. The mixture was made basic with solid NaHCO3 then diluted with EtOAc and water. The layers were separated and the organics were washed with saturated aqueous NaHCO3, water and brine. The solution was dried over Na2SO4 and concentrated in vacuo to give 2-(4-(dimethylamino)phenyl)-2-hydroxyacetonitrile as an off-white solid (5.2 g, quantitative yield). The product was used without further purification.

Quelle