Reaktion #1848

Reaktionsgleichung

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

potassium acetate

t-butyl acrylate

ether

→

t-Butyl 3-{6-hydroxymethyl-3-[8(4-methoxyphenyl)octyloxy]pyridin-2-yl}propenoate

Lösungsmittel

DMF

water

dichloromethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled
2. 2
   ExtraktionThe product was extracted into ethyl acetate (2×60 ml)
3. 3
   WaschenThe combined extracts were washed with water (100 ml), 5% sodium chloride solution (2×100 ml)
4. 4
   Sonstigedried
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe product was obtained by flash column chromatography

Vorschrift

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 (3.00 g, 30.6 mmol), tetra-n-butylammonium iodide (4.36 g, 11.8 mmol), bis(triphenylphosphine)palladium dichloride (0.33 g, 0.47 mmol) and t-butyl acrylate (6.16 g, 48 mmol). The mixture was placed under nitrogen and stirred and heated at 120° C. for 45 min. The mixture was cooled and added to water (250 ml). The product was extracted into ethyl acetate (2×60 ml). The combined extracts were washed with water (100 ml), 5% sodium chloride solution (2×100 ml), then dried and evaporated. The product was obtained by flash column chromatography using silica and 10% ether in dichloromethane. Yield 4.29 g, 77%.

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