反応 #162042

反応方程式

18-crown-6

KOH

acrylonitrile

Cholestanol

→

product

収率 80.0%

3-(Cholestan-3-yloxy)propanenitrile

収率 80.0%

溶媒

DCM

反応条件

後処理

1. 1
   洗浄The organic layer was washed with brine
2. 2
   乾燥dried (Na2SO4) before the solvent
3. 3
   その他was evaporated
4. 4
   その他The residue was recrystallized from hot MeOH

実験手順

Cholestanol (1.554 g, 3.998 mmol) was dissolved in DCM (6 mL). To this solution was added KOH (40% w/w in water, 1.2 mL) and acrylonitrile (0.8 mL), followed by 18-crown-6 (104 mg). The mixture was stirred at room temperature overnight. The organic layer was washed with brine and dried (Na2SO4) before the solvent was evaporated. The residue was recrystallized from hot MeOH to yield the pure product as a colourless crystalline solid (1.42 g, 80% yield). 1H NMR (400 MHz, CDCl3) δ: 3.68 (t, 2H, CH2O), 3.29 (m, 1H, CHO), 2.57 (t, 2H, CH2CN), 1.98-0.58 (m, 31H), 0.89 (d, 3H, J=6.6, CH3), 0.87 (d, 3H, J=1.8, CH3), 0.85 (d, 3H, J=2.0, CH3), 0.79 (s, 3H, CH3), 0.64 (s, 3H, CH3).

出典