Pyridine → HCID 13193770, compound

Participants

Reaction Conditions

Reaction Steps

In a manner similar to that described in the preceding examples, 1.45 grams of 80 percent pyridinium bromide perbromide was added to a cooled to 0° C. solution of 1.00 gram (3.02 millimoles) of dimethyl 2,6-dimethyl-4(2-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate and 0.40 milliliter of pyridine in 20 milliliters of chloroform. The mixture was then stirred at 0° C. for about 30 minutes and at reflux temperature for about 90 minutes. Thereafter the mixture was allowed to cool, diluted with chloroform, washed with 2N hydrochloric acid and brine, dried and the solvent evaporated to obtain a crude product residue. The latter was flash chromatographed on 35 grams of silica gel to obtain 510 milligrams (54 percent yield) of purified methyl 2-methyl-4-(2-methoxyphenyl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylate product. A portion of the product was recrystallized from ethyl acetate-hexane for elemental analyses which were as follows:

Provenance & Evidence