تفاعل #66364

معادلة التفاعل

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

المردود 98.1%

المذيبات

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر