3-(chloromethoxy)prop-1-ene

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 10 ml. of tetrahydrofuran was dissolved 1.0 g. of diethyl 2,6-dimethyl-4-(3-nitrophenyl)-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 30 minutes at room temperature. After cooling the mixture to -10° C., 0.5 ml. of 3-chloromethoxy-1-propene was added thereto, the temperature was elevated to room temperature over a period of about 20 minutes, and then after 15 minutes the mixture was cooled again 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 then ether was distilled away. The residue was subjected to a silica gel column chromatography using benzene as an eluant. The effluent was then subjected to a thin layer chromatography, and then the effluent or the main fraction was concentrated to provide a white crystalline material. By recrystallizing the crystals from benzene-hexane, 0.74 g. of diethyl 1-allyloxymethyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate melting at 111°-112° C. were obtained. after 15 minutes the mixture was cooled again to -10° C of water, the product was extracted three times each time with 5 ml at room temperature washed with 5 ml of saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate ether was distilled away the effluent or the main fraction was concentrated to provide a white crystalline material By recrystallizing the crystals from benzene-hexane, 0.74 g

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 10 ml. of tetrahydrofuran was dissolved 1.0 g. of diethyl 2,6-dimethyl-4-(3-nitrophenyl)-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 30 minutes at room temperature. After cooling the mixture to -10° C., 0.5 ml. of 3-chloromethoxy-1-propene was added thereto, the temperature was elevated to room temperature over a period of about 20 minutes, and then after 15 minutes the mixture was cooled again 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 then ether was distilled away. The residue was subjected to a silica gel column chromatography using benzene as an eluant. The effluent was then subjected to a thin layer chromatography, and then the effluent or the main fraction was concentrated to provide a white crystalline material. By recrystallizing the crystals from benzene-hexane, 0.74 g. of diethyl 1-allyloxymethyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate melting at 111°-112° C. were obtained. after 15 minutes the mixture was cooled again to -10° C of water, the product was extracted three times each time with 5 ml at room temperature washed with 5 ml of saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate ether was distilled away the effluent or the main fraction was concentrated to provide a white crystalline material By recrystallizing the crystals from benzene-hexane, 0.74 g