反応 #351968

反応方程式

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

溶媒

DMF

water

反応条件

後処理

1. 1
   温度The mixture was cooled
2. 2
   ろ過solids filtered
3. 3
   洗浄washed with ethyl acetate (2×60 ml)
4. 4
   洗浄The filtrate was washed with water (250 ml) and with 5% sodium chloride solution (2×125 ml)
5. 5
   その他The organic layer was dried
6. 6
   その他evaporated
7. 7
   その他The pure product was obtained by flash column chromatography (silica, 2,0% ether in dichloromethane) (3.52 g, 72%)
8. 8
   その他mp 112°114° C.

実験手順

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.

出典