反応 #62293

反応方程式

N-formylpiperidine

N,N-diisopropylamine

n-butyllithium

4-fluoro-2-methoxybenzonitrile

→

title compound

収率 37.2%

4-Fluoro-3-formyl-2-methoxybenzonitrile

収率 37.2%

溶媒

tetrahydrofuran

n-hexane

tetrahydrofuran

acetic acid

water

反応条件

後処理

1. 1
   workup.STIRRINGAfter stirring at this temperature for 2 hours
2. 2
   workup.STIRRINGAfter stirring at this temperature for 40 minutes
3. 3
   抽出extracted three times with diethyl ether
4. 4
   洗浄The organic layer was washed successively with 0.2N hydrochloric acid, water and saturated brine
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   その他The solvent was evaporated
7. 7
   その他the crude product was purified
8. 8
   その他separated by silica gel column chromatography

実験手順

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.

出典