تفاعل #351968

معادلة التفاعل

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

المذيبات

DMF

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was cooled
2. 2
   ترشيحsolids filtered
3. 3
   غسيلwashed with ethyl acetate (2×60 ml)
4. 4
   غسيلThe filtrate was washed with water (250 ml) and with 5% sodium chloride solution (2×125 ml)
5. 5
   أخرىThe organic layer was dried
6. 6
   أخرىevaporated
7. 7
   أخرىThe pure product was obtained by flash column chromatography (silica, 2,0% ether in dichloromethane) (3.52 g, 72%)
8. 8
   أخرىmp 112°114° C.

الإجراء التجريبي

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.

المصدر