Hydrogen Peroxide → 3-(4-Cyanophenyl)-2,6-dimethyl-4-(phenylmethoxy)pyridine

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Reaction Steps

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).

Provenance & Evidence