4,5-Dihydro-2-[2-(2-methoxy-5-nitrophenyl)ethenyl]-4,4-dimethyloxazole → 3-[2-(4,5-Dihydro-4,4-dimethyl-2-oxazolyl)ethyl]-4-methoxybenzenamine

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Reaction Steps

Raney nickel, 3 g, is added to a solution of 4,5-dihydro-2-[2-(2-methoxy-5-nitrophenyl)ethenyl]-4,4-dimethyloxazole, 10.9 g, in methanol, 500 ml. The mixture is exposed to hydrogen gas until the appropriate quantity of hydrogen is taken up, filtered and the solvent evaporated to give 10.2 g of 3-[2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)ethyl]-4-methoxybenzenamine as a gum. To an ice cold solution of the previous crude gum and 7 ml of triethylamine in chloroform is added 10.5 g of 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoyl chloride (U.S. Pat. No. 4,285,951). The mixture is worked up, chromatographed over silica gel and eluted with diethylether to give 10.5 g of N-[3-[2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)ethyl]-4-methoxyphenyl]-5-(2,5-dimethylphenoxy)-2,2-dimethylpentanamide as a gum; thin layer chromatography on silica gel: Rf =0.57 (ethyl acetate).

Provenance & Evidence