Réaction #2388664

Équation de réaction

1-bromo-3,5-dimethyladamantane

acrylonitrile

tri-n-butyltin hydride

→

product

Rendement 86.3%

3-(3, 5-Dimethyl-1-adamantyl)propionitrile

Rendement 86.3%

Solvants

toluene

ether

Conditions de réaction

Traitement

1. 1
   Températurerefluxed for 3.5 h
2. 2
   Températurecooled
3. 3
   Lavagewashed with 0.2-M NH4OH (30 mL), water (10 mL)
4. 4
   Séchagedried (MgSO4)
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe residue was purified by chromatography [SiO2, CH2Cl2-hexane (0:100 to 100:0)]

Mode opératoire

A solution of 1-bromo-3,5-dimethyladamantane (1.0 g, 4.11 mmol), acrylonitrile (436 mg, 8.22 mmol) and 1,1′-azobis(cyclohexanecarbonitrile) (50 mg, 0.21 mmol) in dry toluene (12 mL) was treated with tri-n-butyltin hydride (1.44 g, 4.93 mmol) at room temperature, refluxed for 3.5 h, cooled, diluted with ether (30 mL), washed with 0.2-M NH4OH (30 mL), water (10 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography [SiO2, CH2Cl2-hexane (0:100 to 100:0)] to give the product (771 mg, 86%) as a colourless oil: IR νmax (liquid film)/cm−1 2899, 2841, 2247, 1545 and 1359; NMR δH (400 MHz, CDCl3) 0.81 (6H, s), 1.0-1.2 (6H, m), 1.25-1.35 (6H, m), 1.53 (2H, t, J 4.2 Hz), 2.05-2.10 (1H, m) and 2.27 (2H, tJ 4.2 Hz).

Source