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0 °C

4-[3-(3-Benzyloxy-2-pyridyl)prop-2-enyl)benzoic acid (0.1 g, 0.29 mmol) was dissolved in methanol (5 ml) and cooled to 0° C. To the solution was added thionyl chloride (0.086 g, 0.73 mmol). The reaction was allowed to warm to ambient temperature and stirred at ambient temperature for 18 hours. The reaction mixture was then evaporated, the residue partitioned between ethyl acetate and water and the organic phase dried (MgSO4) and evaporated. The residue was purified by chromatography (SiO2 EtOAc/CH2Cl2) to give methyl 4-[3-(3-benzyloxy-2-pyridyl)prop-2-enyl]benzoate as an oil (0.05 g, 49%).

1. temperatureto warm to ambient temperature
2. customThe reaction mixture was then evaporated
3. customthe residue partitioned between ethyl acetate and water
4. dry with materialthe organic phase dried (MgSO4)
5. customevaporated
6. customThe residue was purified by chromatography (SiO2 EtOAc/CH2Cl2)