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

Temperature

120 °C

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.

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

ORD record

ord-d167806c04b646d4b1c49664d0f6f7f3

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05726315