반응 #62293

반응 방정식

N-formylpiperidine

N,N-diisopropylamine

n-butyllithium

4-fluoro-2-methoxybenzonitrile

→

title compound

수율 37.2%

4-Fluoro-3-formyl-2-methoxybenzonitrile

수율 37.2%

용매

tetrahydrofuran

n-hexane

tetrahydrofuran

acetic acid

water

반응 조건

후처리

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

실험 절차

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.

출처