反应详情

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).

1. customThe mixture was placed under a drying tube
2. stirringthe mixture stirred for 24 hrs more
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with CH2Cl2
5. washThe combined organics were washed with brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated in vacuo
8. customPurification by chromatography (20-35% EtOAc-hexanes containing 1% Et3N)