Tetrahydrofuran → HCID 21437225, compound

Participants

Reaction Conditions

Reaction Steps

In 10 ml. of tetrahydrofuran was dissolved 0.5 g. of diethyl 4-(3-nitrophenyl)-2,6-dipropyl-1,4-dihydropyridine-3,5-dicarboxylate and after adding to the solution 0.2 g. of a 50% oil dispersion of sodium hydride, the mixture was stirred for 2 hours at room temperature. After cooling the mixture to -20° C., 0.5 ml. of chloromethoxyethane was added thereto and the mixture reacted for 1.5 hours at temperatures of from -20° C. to -10° C. After adding to the reaction product 0.5 ml. of glacial acetic acid and 20 ml. of water, the product was extracted three times each time with 5 ml. of ether at room temperature. The extracts were combined, washed with 5 ml. of saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and the ether was distilled away. The residue was subjected to a silica gel column chromatography, using a 10:1 benzene-acetone mixed solvent as an eluant, the effluent thus recovered was examined by a thin layer chromatography, and the effluent of the main fraction recovered was concentrated. By recrystallizing the residue formed from hexane, 0.4 g. of colorless acicular crystals of diethyl 1-ethoxymethyl-4-(3-nitrophenyl)-2,6-dipropyl-1,4-dihydropyridine-3,5-dicarboxylate melting at 109°-110° C. were obtained.

Provenance & Evidence