反応 #84859

反応方程式

NaHCO3

ethylvinyl ether

pyridinium para-toluenesulfonate

2-hydroxy-3-methoxy-3-(4-morpholinophenyl)propanenitrile

pyridinium para-toluenesulfonate

ethyl vinyl ether

→

2-(1-ethoxyethoxy)-3-methoxy-3-(4-morpholinophenyl)propanenitrile

収率 35.5%

溶媒

H2O

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   その他The mixture was placed under a drying tube
2. 2
   workup.STIRRINGthe mixture stirred for 24 hrs more
3. 3
   その他The layers were separated
4. 4
   抽出the aqueous layer was extracted with CH2Cl2
5. 5
   洗浄The combined organics were washed with brine
6. 6
   乾燥dried over MgSO4
7. 7
   濃縮concentrated in vacuo
8. 8
   その他Purification by chromatography (20-35% EtOAc-hexanes containing 1% Et3N)

実験手順

To a solution of 2-hydroxy-3-methoxy-3-(4-morpholinophenyl)propanenitrile (˜5.1 mmol) in anhydr CH2Cl2 (17 mL) under argon was added pyridinium para-toluenesulfonate (0.094 g, 0.37 mmol) and ethyl vinyl ether (17 mL, 178 mmol). The mixture was placed under a drying tube and stirred at room temperature for 16 hrs. Additional ethylvinyl ether (4 mL, 42 mmol) and pyridinium para-toluenesulfonate (0.11 g, 0.44 mmol) were added and the mixture stirred for 24 hrs more. Saturated aqueous NaHCO3 was added to the mixture then it was diluted with H2O and CH2Cl2. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organics were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by chromatography (20-35% EtOAc-hexanes containing 1% Et3N) gave 2-(1-ethoxyethoxy)-3-methoxy-3-(4-morpholinophenyl)propanenitrile (0.606 g, 35% for three steps).

出典