Reaktion #86068

Reaktionsgleichung

cyclopentanecarboxylic acid ethyl ester

hydrochloric acid

sodium hydride

acetonitrile

→

3-cyclopentyl-3-oxo-propionitrile

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring for 30 min at room temperature
2. 2
   Temperaturthe mixture was heated at 105° C. during 16 h
3. 3
   TemperaturAfter cooling
4. 4
   Sonstigethe solvent was evaporated to dryness and water
5. 5
   workup.ADDITIONwas added (30 mL)
6. 6
   ExtraktionThe mixture was extracted with dichloromethane (3×30 mL)
7. 7
   Sonstigeto get rid of the starting material
8. 8
   Extraktionextracted with dichloromethane (3×30 mL)
9. 9
   TrocknenThe combined organic phases were dried over magnesium sulfate
10. 10
    Filtrationfiltered
11. 11
    Sonstigedried in vacuo

Vorschrift

To a suspension of sodium hydride (350 mg, 8.8 mmol, 1.2 eq) in 1,4-dioxane (10 mL) was added acetonitrile (450 μL, 8.8 mmol, 1.2 eq). The mixture was stirred at room temperature for 30 min. Then cyclopentanecarboxylic acid ethyl ester (660 μL, 7.3 mmol, 1 eq) was added. After stirring for 30 min at room temperature, the mixture was heated at 105° C. during 16 h. After cooling, the solvent was evaporated to dryness and water was added (30 mL). The mixture was extracted with dichloromethane (3×30 mL) to get rid of the starting material and the aqueous phase was acidified with a 1N solution of hydrochloric acid and extracted with dichloromethane (3×30 mL). The combined organic phases were dried over magnesium sulfate, filtered and dried in vacuo to afford 3-cyclopentyl-3-oxo-propionitrile as very volatile yellow oil (1.0 g, quant. yield)

Quelle