1,1-Dimethylhydrazine → 3-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid N',N'-dimethyl-hydrazide

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Reaction Steps

A solution of trimethylaluminium (2 M in toluene, 0.6 mL, 1.3 mmol) was added dropwise (exothermic) to a solution of N,N-dimethylhydrazine (76 mg, 1.3 mmol) in dioxane (5 mL) and the resulting mixture was stirred at room temperature for 1 h. Then 3-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester (100 mg, 0.32 mmol) was added. The resulting mixture was then heated at 85-90° C. for 4 h and then cooled to room temperature and then poured into Seignette's salt and extracted with ethyl acetate which was then washed with brine, dried over sodium sulfate and evaporated. Purification by chromatography (silica, dichloromethane:methanol=9:1 to 4:1) afforded the title compound (24 mg, 22%) which was obtained as a colourless oil. MS: m/e=343.3 [M+H]+.

Provenance & Evidence