반응 #351968

반응 방정식

2-bromo-6-hydroxymethyl-[8(4-methoxyphenyl)octyloxy]pyridine

potassium acetate

triphenylphosphine

potassium acrylate

potassium acrylate

→

3-{6-Hydroxymethyl-3-[8(4-methoxyphenyl)octyloxy]pyridin-2-yl}propenoic Acid

용매

DMF

water

반응 조건

후처리

1. 1
   온도The mixture was cooled
2. 2
   여과solids filtered
3. 3
   세척washed with ethyl acetate (2×60 ml)
4. 4
   세척The filtrate was washed with water (250 ml) and with 5% sodium chloride solution (2×125 ml)
5. 5
   기타The organic layer was dried
6. 6
   기타evaporated
7. 7
   기타The pure product was obtained by flash column chromatography (silica, 2,0% ether in dichloromethane) (3.52 g, 72%)
8. 8
   기타mp 112°114° C.

실험 절차

To a solution of 2-bromo-6-hydroxymethyl-[8(4-methoxyphenyl)octyloxy]pyridine (5.00 g, 11.8 mmol) in DMF (22.8 ml) and water (1.2 ml) were added potassium acetate (2.91 g, 29.7 mmol), tetra-n-butylammonium iodide (4.37 g, 11.8 mmol), triphenylphosphine (0,245 g, 0.94 mmol), palladium chloride (83 mg, 0.47 mmol) and potassium acrylate (3.91 g, 35.4 mmol). The mixture was placed under nitrogen and stirred and heated at 120° C. for 3.3 h. Some potassium acrylate remained undissolved. The mixture was cooled, solids filtered and washed with ethyl acetate (2×60 ml). The filtrate was washed with water (250 ml) and with 5% sodium chloride solution (2×125 ml). The organic layer was dried and evaporated. The pure product was obtained by flash column chromatography (silica, 2,0% ether in dichloromethane) (3.52 g, 72%). mp 112°114° C.

출처