反应详情

A solution of compound C (188 mg) in methanol (1 ml) was added to a mixture of compound B (170 mg), tetrakis(triphenylphosphine)palladium (30 mg), 2M sodium hydrogen carbonate solution (2 ml) and toluene (10 ml). The mixture was heated under reflux for 12 hours and then allowed to cool. Hydrogen peroxide solution (30 wt. % solution in water; 0.1 ml) was added and the mixture was stirred for 30 minutes. The aqueous phase was separated and extracted with ethyl acetate (2×25 ml). The combined organic solutions were dried (MgSO4) and volatile material was removed by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (4:1 v/v) to give 3-(4-cyanophenyl)-2,6-dimethyl-4-(phenylmethoxy)pyridine (D), as a gum; NMR (CDCl3): 2.3(s,3H), 2.6(s,3H), 5.1(s,2H), 6.7(s,1H), 7.1-7.2(m,2H), 7.25-7.35(m,5H), 7.7(d,2H).

1. temperatureThe mixture was heated
2. temperatureunder reflux for 12 hours
3. temperatureto cool
4. customThe aqueous phase was separated
5. extractionextracted with ethyl acetate (2×25 ml)
6. dry with materialThe combined organic solutions were dried (MgSO4) and volatile material
7. customwas removed by evaporation
8. customThe residue was purified by flash chromatography
9. washeluting with ethyl acetate/hexane (4:1 v/v)