반응 #66364

반응 방정식

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

수율 98.1%

용매

THF

반응 조건

후처리

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

실험 절차

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%).

출처