Sodium hydride → HCID 13240321, compound

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Reaction Steps

0.24 g (10 mmole) of sodium hydride was suspended in 10 ml of dimethylsulfoxide, to which was added gradually 1.95 g (10 mmole) of 3-o-chlorophenyl-5-pyrazolone with stirring at room temperature. After evolution of hydrogen had ceased, to this solution was added 10 ml of a solution of 6.01 g (10 mmole) of 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3-ethoxycarbonylpyridine-5-carboxylic acid 6-tosyloxyhexyl ester in dimethylsulfoxide, and stirring with heating at 80° C. was continued for an hour. The resultant reaction mixture was poured into 150 ml of ice water, and the separated product was extracted with 50 ml of chloroform. This chloroform solution was washed with 50 ml of water 4 times, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a brown oily residue. This residue was purified by chromatography on a silica gel column using a mixed solution of chloroform-methanol (the ratio by volume of 100:1) as an eluent, and further by chromatography on a silica gel column eluting with a toluene-ethyl acetate mixed solution, and the eluate fractions containing the purified intended compound were concentrated to dryness under reduced pressure to obtain 2.55 g (yield 40.9%) of the 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3-ethoxycarbonylpyridine-5-carboxylic acid 6-(5-o-chlorophenyl-3-pyrazolyloxy)hexyl ester as a pale yellow powder.

Provenance & Evidence