반응 #1964345

반응 방정식

5-bromo-2-methylfuran-3-carbaldehyde

5-methyl-3-pyridineboronic acid

sodium carbonate

1,2-dimethoxyethane

→

title compound

수율 81.0%

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

수율 81.0%

용매

water

반응 조건

후처리

1. 1
   온도with refluxing under an argon atmosphere
2. 2
   추출the mixture was extracted with ethyl acetate
3. 3
   세척The organic layer was washed with saturated brine
4. 4
   건조dried over magnesium sulfate
5. 5
   기타The solvent was evaporated under reduced pressure
6. 6
   기타The residue was purified by silica gel chromatography (10% ethyl acetate/hexane to 50% ethyl acetate/hexane)
7. 7
   기타crystallized from ethyl acetate/hexane

실험 절차

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.

출처