4-(2-iodoethyl)-1,2-dimethoxybenzene

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-hydroxy-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one (844 mg, 4.35 mmol) in dimethylformamide (5 ml) was stirred while 60% oily sodium hydride (191 mg, 4.78 mg) in small portions were added thereto. Subsequently, 3,4-dimethoxyphenethyl iodide (2.54 mg, 8.70 mmol) was added, then the solution was heated at 80° C. for 7 hours. The solution was diluted with dichloromethane, washed with water and dried over sodium sulfate. After solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography [eluent:hexane/ethyl acetate (3:2)] to give 169 mg of 2-[2-(3,4-dimethoxyphenyl)ethoxy]-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one as a yellowish brown oil (yield: 11%). were added washed with water dried over sodium sulfate After solvent was distilled off under reduced pressure the residue was purified by silica gel column chromatography [eluent:hexane/ethyl acetate (3:2)]

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a flask under argon containing 4.94 g (0.0119 mole) diltiazem was added 50 ml ethyl acetate and 3.48 g (0.0119 mole) 3,4-dimethoxyphenethyl iodide. The reaction was refluxed for 24 hr then filtered. The filtrate was washed with sodium bicarbonate and brine, dried over K2CO3, and 0.85 g 3,4-dimethoxyphenethyl iodide added and the reaction refluxed for 18 hr then filtered. The last step was repeated but 1.75 g of 3,4-dimethoxyphenethyl iodide was added and the reaction refluxed 5 hr. The filtered materials were combined and recrystallized from 95% ethanol to give a mixture of product and diltiazem hydroiodide. The reaction was refluxed for 24 hr then filtered The filtrate was washed with sodium bicarbonate and brine dried over K2CO3, and 0.85 g 3,4-dimethoxyphenethyl iodide added the reaction refluxed for 18 hr then filtered 1.75 g of 3,4-dimethoxyphenethyl iodide was added the reaction refluxed 5 hr recrystallized from 95% ethanol to give

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a flask was added 21.2 g (0.078 mole) of 2-(3,4-dimethoxyphenyl)ethyl methanesulfonate and 44.65 g (0.3 mole) of sodium iodide in 420 ml of acetone. The solution was refluxed for 2 hr, poured into water, washed with brine, dried over MgSO4, and evaporated to give 21.1 g of a yellow oil. The oil was recrystallized in MeOH to give 17.1 g of product, mp 43°-46° C. The solution was refluxed for 2 hr washed with brine dried over MgSO4 evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a flask was added 21.2 g (0.078 mole) of 2-(3,4-dimethoxyphenyl)ethyl methanesulfonate and 44.65 g (0.3 mole) of sodium iodide in 420 ml of acetone. The solution was refluxed for 2 hr, poured into water, washed with brine, dried over MgSO4, and evaporated to give 21.1 g of a yellow oil. The oil was recrystallized in MeOH to give 17.1 g of product, mp 43°-46° C. The solution was refluxed for 2 hr washed with brine dried over MgSO4 evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-(2-Iodoethyl)-3,4-dimethoxybenzene (29.3 g.) and 4-acetamidopyridine (14.0 g.) in absolute ethanol (100 ml.) were refluxed for 2.5 hours. The resulting crystalline material was collectd and recrystallised from ethanol to give the title compound (29.1 g.), m.p. 201°-202° C. (Found: C, 47.9; H, 4.9; N, 6.3; C17H21IN2O3 requires C, 47.7; H, 4.9; N, 6.5%). recrystallised from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-(2-Iodoethyl)-3,4-dimethoxybenzene (29.3 g.) and 4-acetamidopyridine (14.0 g.) in absolute ethanol (100 ml.) were refluxed for 2.5 hours. The resulting crystalline material was collectd and recrystallised from ethanol to give the title compound (29.1 g.), m.p. 201°-202° C. (Found: C, 47.9; H, 4.9; N, 6.3; C17H21IN2O3 requires C, 47.7; H, 4.9; N, 6.5%). recrystallised from ethanol

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-hydroxy-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one (844 mg, 4.35 mmol) in dimethylformamide (5 ml) was stirred while 60% oily sodium hydride (191 mg, 4.78 mg) in small portions were added thereto. Subsequently, 3,4-dimethoxyphenethyl iodide (2.54 mg, 8.70 mmol) was added, then the solution was heated at 80° C. for 7 hours. The solution was diluted with dichloromethane, washed with water and dried over sodium sulfate. After solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography [eluent:hexane/ethyl acetate (3:2)] to give 169 mg of 2-[2-(3,4-dimethoxyphenyl)ethoxy]-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one as a yellowish brown oil (yield: 11%). were added washed with water dried over sodium sulfate After solvent was distilled off under reduced pressure the residue was purified by silica gel column chromatography [eluent:hexane/ethyl acetate (3:2)]

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-(2-Iodoethyl)-3,4-dimethoxybenzene (29.3 g.) and 4-acetamidopyridine (14.0 g.) in absolute ethanol (100 ml.) were refluxed for 2.5 hours. The resulting crystalline material was collected and recrystallised from ethanol to give the title compound (29.1 g.)., m.p. 201°-202° C. (Found: C, 47.9; H, 4.9; N, 6.3; C17H21IN2O3 requires C, 47.7; H, 4.9; N, 6.5%). The resulting crystalline material was collected recrystallised from ethanol

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-hydroxy-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one (844 mg, 4.35 mmol) in dimethylformamide (5 ml) was stirred while 60% oily sodium hydride (191 mg, 4.78 mg) in small portions were added thereto. Subsequently, 3,4-dimethoxyphenethyl iodide (2.54 mg, 8.70 mmol) was added, then the solution was heated at 80° C. for 7 hours. The solution was diluted with dichloromethane, washed with water and dried over sodium sulfate. After solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (3:2)] to give 169 mg of 2-[2-(3,4-dimethoxyphenyl)ethoxy]-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one as a yellowish brown oil (yield: 11%). were added washed with water dried over sodium sulfate After solvent was distilled off under reduced pressure the residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (3:2)]