Reaction #1849

Reaction equation

potassium acrylate

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

potassium acetate

potassium acrylate

triphenylphosphine

→

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

Solvents

DMF

water

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled
2. 2
   Filtrationsolids filtered
3. 3
   Washwashed with ethyl acetate (2×60 ml)
4. 4
   WashThe filtrate was washed with water (250 ml) and with 5% sodium chloride solution (2×125 ml)
5. 5
   OtherThe organic layer was dried
6. 6
   Otherevaporated
7. 7
   OtherThe pure product was obtained by flash column chromatography (silica, 20% ether in dichloromethane) (3.52 g, 72%)

Procedure

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, 20% ether in dichloromethane) (3.52 g, 72%). mp 112°-114° C.

Source