تفاعل #1136751

معادلة التفاعل

(E)-ethyl 3-(3-((methoxymethoxy)methyl)phenyl)acrylate

n-butyllithium

diisopropylamine

isobutyronitrile

→

title compound

ethyl 4-cyano-3-(3-((methoxymethoxy)methyl)phenyl)-4-methylpentanoate

المذيبات

hexane

THF

Water

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 20 min
2. 2
   استخلاصthe mixture was extracted with ethyl acetate
3. 3
   غسيلThe extract was washed with water and saturated brine
4. 4
   تجفيفdried over anhydrous magnesium sulfate
5. 5
   أخرىThe solvent of the reaction mixture was evaporated under reduced pressure
6. 6
   أخرىthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

الإجراء التجريبي

Under a nitrogen atmosphere, a solution (1.6 M, 1.50 mL) of n-butyllithium in hexane was added to a solution of diisopropylamine (336 μL) in THF (2 mL) at −78° C., to the reaction mixture was added isobutyronitrile (227 μL) at −78° C., and the mixture was stirred for 5 min. To the reaction mixture was added (E)-ethyl 3-(3-((methoxymethoxy)methyl)phenyl)acrylate (250 mg) at −78° C., and the mixture was stirred at room temperature for 20 min. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent of the reaction mixture was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (210 mg) as a colorless oil.

المصدر