تفاعل #1964345

معادلة التفاعل

5-bromo-2-methylfuran-3-carbaldehyde

5-methyl-3-pyridineboronic acid

sodium carbonate

1,2-dimethoxyethane

→

title compound

المردود 81.0%

5-(5-methylpyridin-3-yl)-2-methylfuran-3-carbaldehyde

المردود 81.0%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwith refluxing under an argon atmosphere
2. 2
   استخلاصthe mixture was extracted with ethyl acetate
3. 3
   غسيلThe organic layer was washed with saturated brine
4. 4
   تجفيفdried over magnesium sulfate
5. 5
   أخرىThe solvent was evaporated under reduced pressure
6. 6
   أخرىThe residue was purified by silica gel chromatography (10% ethyl acetate/hexane to 50% ethyl acetate/hexane)
7. 7
   أخرىcrystallized from ethyl acetate/hexane

الإجراء التجريبي

A mixture of 5-bromo-2-methylfuran-3-carbaldehyde (1.9 g), 5-methyl-3-pyridineboronic acid (1.6 g), tetrakis(triphenylphosphine)palladium(0) (0.6 g), 2N aqueous sodium carbonate solution (12 mL) and 1,2-dimethoxyethane (20 mL) was stirred overnight with refluxing under an argon atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (10% ethyl acetate/hexane to 50% ethyl acetate/hexane), and crystallized from ethyl acetate/hexane to give the title compound (1.6 g, 81%) as a white crystal.

المصدر