反应 #74102

反应方程式

Pyridine-4-carbaldehyde

water

Sodium hydride

[(3-cyano-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]phosphonic acid dimethyl ester

pyridine-4-carbaldehyde

→

3-[(E)-2-Pyridin-4-yl-1-(tetrahydro-pyran-2-yloxy)-vinyl]-benzonitrile

收率 98.1%

溶剂

THF

反应条件

后处理

1. 1
   workup.STIRRINGthe reaction mixture was stirred at 50° C. for 3 h under nitrogen atmosphere
2. 2
   其他the solvent (THF) was removed under reduced pressure
3. 3
   萃取The water layer was extracted with EtOAc (3×100 ml), DCM (1×100 ml)
4. 4
   干燥the organic layers were dried over Na2SO4
5. 5
   其他The filtrate was evaporated to dryness

实验过程

Sodium hydride (2.28 g, 94.98 mmol) was added to a solution of [(3-cyano-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]phosphonic acid dimethyl ester (20.58 g, 63.3 mmol) in dry THF and the mixture was stirred at room temperature for 15′. Pyridine-4-carbaldehyde (6.78 g, 63.3 mmol) was then added and the reaction mixture was stirred at 50° C. for 3 h under nitrogen atmosphere. In order to affect completion a further addition of pyridine-4-carbaldehyde (0.68 g, 6.33 mmol) was required. Distilled water (40 ml) was slowly poured into the reaction mixture and the solvent (THF) was removed under reduced pressure. The water layer was extracted with EtOAc (3×100 ml), DCM (1×100 ml) and the organic layers were dried over Na2SO4. The filtrate was evaporated to dryness to give the crude product 3-[(E)-2-Pyridin-4-yl-1-(tetrahydro-pyran-2-yloxy)-vinyl]-benzonitrile as a brown oil (19.0 g, 62.10 mmol, 98%).

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