Реакция #84859

Уравнение реакции

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

Выход 35.5%

Растворители

H2O

CH2Cl2

CH2Cl2

Условия реакции

Обработка

1. 1
   ДругоеThe mixture was placed under a drying tube
2. 2
   workup.STIRRINGthe mixture stirred for 24 hrs more
3. 3
   ДругоеThe layers were separated
4. 4
   Экстракцияthe aqueous layer was extracted with CH2Cl2
5. 5
   ПромывкаThe combined organics were washed with brine
6. 6
   Сушкаdried over MgSO4
7. 7
   Концентрированиеconcentrated in vacuo
8. 8
   ДругоеPurification by chromatography (20-35% EtOAc-hexanes containing 1% Et3N)

Методика

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).

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