Réaction #62293

Équation de réaction

N-formylpiperidine

N,N-diisopropylamine

n-butyllithium

4-fluoro-2-methoxybenzonitrile

→

title compound

Rendement 37.2%

4-Fluoro-3-formyl-2-methoxybenzonitrile

Rendement 37.2%

Solvants

tetrahydrofuran

n-hexane

tetrahydrofuran

acetic acid

water

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGAfter stirring at this temperature for 2 hours
2. 2
   workup.STIRRINGAfter stirring at this temperature for 40 minutes
3. 3
   Extractionextracted three times with diethyl ether
4. 4
   LavageThe organic layer was washed successively with 0.2N hydrochloric acid, water and saturated brine
5. 5
   Séchagedried over anhydrous magnesium sulfate
6. 6
   AutreThe solvent was evaporated
7. 7
   Autrethe crude product was purified
8. 8
   Autreseparated by silica gel column chromatography

Mode opératoire

Under nitrogen atmosphere and at −78° C., to a solution of 10.7 g of N,N-diisopropylamine in 150 mL of tetrahydrofuran was added 40 mL of 2.66 M n-butyllithium in n-hexane, stirred at this temperature for 1 hour and 15 minutes, and added dropwise with a solution of 14.5 g of 4-fluoro-2-methoxybenzonitrile obtained by Production example 95 in 50 mL of tetrahydrofuran. After stirring at this temperature for 2 hours, 11.94 g of N-formylpiperidine was added. After stirring at this temperature for 40 minutes, the solution was added with 20 mL of acetic acid at this temperature, added with water at room temperature, and extracted three times with diethyl ether. The organic layer was washed successively with 0.2N hydrochloric acid, water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography, to afford 6.4 g of the title compound 6.4 g as pale yellow crystals.

Source