1-iodo-4-propylbenzene

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

実験手順: As described in Example 1(d) for the preparation of 4-furan-3-yl-pyridine, 1-iodo-4-propylbenzene (500 mg, 2.03 mmol) was coupled to 3-furanboronic acid to furnish in high yield 3-(4-propylphenyl)-furan as a light brown oil that was unstable and used immediately without further purification. to furnish

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

実験手順: As described in Example 1(d) for the preparation of 4-furan-3-yl-pyridine, 1-iodo-4-propylbenzene (500 mg, 2.03 mmol) was coupled to 3-furanboronic acid to furnish in high yield 3-(4-propylphenyl)-furan as a light brown oil that was unstable and used immediately without further purification. 1H NMR (CDCl3): ∂ 7.69 (t, 1H, J=0.9 Hz), 7.46 (t, 1H, J=1.7 Hz), 7.40 (d, 2H, J=8.1 Hz), 7.18 (d, 2H, J=7.8 Hz), 6.68 (t, 1H, J=0.9 Hz), 2.59 (t, 2H, J=7.5 Hz), 1.66-1.60 (m, 2H), 0.95 (t, 3H, J=7.5 Hz). ##STR91## to furnish

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

実験手順: As described in Example 1(d) for the preparation of 4-furan-3-yl-pyridine, 1-iodo-4-propylbenzene (500 mg, 2.03 mmol) was coupled to 3-furanboronic acid to furnish in high yield 3-(4-propylphenyl)-furan as a light brown oil that was unstable and used immediately without further purification. 1H NMR (CDCl3): ∂ 7.69 (t, 1H, J=0.9 Hz), 7.46 (t, 1H, J=1.7 Hz), 7.40 (d, 2H, J=8.1 Hz), 7.18 (d, 2H, J=7.8 Hz), 6.68 (t, 1H, J=0.9 Hz), 2.59 (t, 2H, J=7.5 Hz), 1.66-1.60 (m, 2H), 0.95 (t, 3H, J=7.5 Hz). ##STR91## to furnish

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

実験手順: As described in Example 1(d) for the preparation of 4-furan-3-yl-pyridine, 1-iodo-4-propylbenzene (500 mg, 2.03 mmol) was coupled to 3-furanboronic acid to furnish in high yield 3-(4-propylphenyl)-furan as a light brown oil that was unstable and used immediately without further purification. 1H NMR (CDCl3): ∂ 7.69 (t, 1H, J=0.9 Hz), 7.46 (t, 1H, J=1.7 Hz), 7.40 (d, 2H, J=8.1 Hz), 7.18 (d, 2H, J=7.8 Hz), 6.68 (t, 1H, J=0.9 Hz), 2.59 (t, 2H, J=7.5 Hz), 1.66-1.60 (m, 2H), 0.95 (t, 3H, J=7.5 Hz). to furnish

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

実験手順: As described in Example 1(d) for the preparation of 4-furan-3-yl-pyridine, 1-iodo-4-propylbenzene (500 mg, 2.03 mmol) was coupled to 3-furanboronic acid to furnish in high yield 3-(4-propylphenyl)-furan as a light brown oil that was unstable and used immediately without further purification. to furnish

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

実験手順: As described in Example 1(d) for the preparation of 4-furan-3-yl-pyridine, 1-iodo-4-propylbenzene (500 mg, 2.03 mmol) was coupled to 3-furanboronic acid to furnish in high yield 3-(4-propylphenyl)-furan as a light brown oil that was unstable and used immediately without further purification. to furnish

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

実験手順: As described in Example 1(d) for the preparation of 4-furan-3-yl-pyridine, 1-iodo-4-propylbenzene (500 mg, 2.03 mmol) was coupled to 3-furanboronic acid to furnish in high yield 3-(4-propylphenyl)-furan as a light brown oil that was unstable and used immediately without further purification. 1H NMR (CDCl3): ∂ 7.69 (t, 1H, J=0.9 Hz), 7.46 (t, 1H, J=1.7 Hz), 7.40 (d, 2H, J=8.1 Hz), 7.18 (d, 2H, J=7.8 Hz), 6.68 (t, 1H, J=0.9 Hz), 2.59 (t, 2H, J=7.5 Hz), 1.66-1.60 (m, 2H), 0.95 (t, 3H, J=7.5 Hz). to furnish

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

実験手順: As described in Example 1(d) for the preparation of 4-furan-3-yl-pyridine, 1-iodo-4-propylbenzene (500 mg, 2.03 mmol) was coupled to 3-furanboronic acid to furnish in high yield 3-(4-propylphenyl)-furan as a light brown oil that was unstable and used immediately without further purification. 1H NMR (CDCl3): ∂ 7.69 (t, 1H, J=0.9 Hz), 7.46 (t, 1H, J=1.7 Hz), 7.40 (d, 2H, J=8.1 Hz), 7.18 (d, 2H, J=7.8 Hz), 6.68 (t, 1H, J=0.9 Hz), 2.59 (t, 2H, J=7.5 Hz), 1.66-1.60 (m, 2H), 0.95 (t, 3H, J=7.5 Hz). to furnish

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

実験手順: Grignard reagent was prepared from 2.43 g (0.10 mol) of dried magnesium and 24.6 g (0.10 mol) of 4-propyliodobenzene in THF, and 100 ml of solution of 21.4 g (0.09 mol) of bicyclohexanedione monoethylene ketal in THF was added dropwise thereto and stirred at room temperature for 3 hours. The reaction solution was added in 300 ml of 3N hydrochloric acid, and the product thus formed was extracted with diethyl ether. After the extract was washed with saturated aqueous sodium bicarbonate solution and water in this turn, the solvent was distilled off under a reduced pressure. To the residue were added 30 ml of toluene and 80 ml of formic acid, and the mixture was refluxed for 3 hours. To the reaction solution was added 100 ml of water and the product thus formed was extracted with toluene. After the extract was washed with saturated aqueous sodium bicarbonate solution and water in this turn, the solvent was distilled off under a reduced pressure. After the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=4/1), the solvent was distilled off to give 9.5 g (32 mmol) of 1-(4-propylphenyl)-4-(4-oxocyclohexyl)-1-cyclohexene. Yield of this compound was 36%. was added dropwise the product thus formed was extracted with diethyl ether After the extract was washed with saturated aqueous sodium bicarbonate solution and water in this turn the solvent was distilled off under a reduced pressure To the residue were added 30 ml of toluene and 80 ml of formic acid the mixture was refluxed for 3 hours To the reaction solution was added 100 ml of water the product thus formed was extracted with toluene After the extract was washed with saturated aqueous sodium bicarbonate solution and water in this turn the solvent was distilled off under a reduced pressure After the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=4/1) the solvent was distilled off

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

実験手順: In 1 l four-necked flask having a gas supplying tube, 200 ml of n-hexane, 75 ml of dry diethyl ether and 24.6 g (0.1 mol) of 4-(n-propyl)iodobenzene were introduced under a nitrogen atmosphere, and then 86.2 ml of a hexane solution of n-butyl lithium (1.16 mol) was dropwise added thereto under stirring at -80° C. Then, while the reaction system was maintained at -80° C., 10 g (0.1 mol) of tetrafluoroethylene was introduced under vigorously stirring in 30 minutes. The reaction solution was stirred further for one hour and poured into ice water and neutralized with dilute hydrochloric acid, and then the organic layer was separated. The aqueous layer was extracted with methylene chloride, and the extract was combined to the organic layer, followed by drying. The solvent was distilled off to obtain 12 g (yield: 60%) of 1-(4-n-propylphenyl)-1,2,2-trifluoroethylene. In 1 l four-necked flask having Then, while the reaction system was maintained at -80° C. under vigorously stirring in 30 minutes The reaction solution was stirred further for one hour the organic layer was separated The aqueous layer was extracted with methylene chloride by drying The solvent was distilled off

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

実験手順: Air in a dried four-necked flask was replaced with nitrogen, and 10 ml of n-hexane and 2.86 g (0.0116 mol) of p-n-propyliodobenzene were introduced. Then, 10 ml of a hexane solution of n-butyl lithium (0.0116 mol) was gradually added thereto under stirring to obtain a hexane solution of n-propylphenyl lithium. were introduced

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

実験手順: As described in Example 1(d) for the preparation of 4-furan-3-yl-pyridine, 1-iodo-4-propylbenzene (500 mg, 2.03 mmol) was coupled to 3-furanboronic acid to furnish in high yield 3-(4-propylphenyl)-furan as a light brown oil that was unstable and used immediately without further purification. 1H NMR (CDCl3): ∂ 7.69 (t, 1H, J=0.9 Hz), 7.46 (t, 1H, J=1.7 Hz), 7.40 (d, 2H, J=8.1 Hz), 7.18 (d, 2H, J=7.8 Hz), 6.68 (t, 1H, J=0.9 Hz), 2.59 (t, 2H, J=7.5 Hz), 1.66-1.60 (m, 2H), 0.95 (t, 3H, J=7.5 Hz). ##STR91## to furnish