2-异丁氧基苯甲醛

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 0.92 g of 60% sodium hydride was suspended in 30 mL of tetrahydrofuran, to which 5.0 mL of ethyl diethylphosphonoacetate was added dropwise over 5 minutes at room temperature, and this mixture was stirred for 30 minutes at 40° C. Then, after 3.40 g of 2-isobutoxybenzaldehyde dissolved in 20 mL of tetrahydrofuran was added to the mixture dropwise over 20 minutes at room temperature, this mixture was stirred for one hour at the same temperature. The reaction mixture was added to a mixture of ethyl acetate and water, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=9:1] to yield 4.30 g of ethyl (E)-3-(2-isobutoxyphenyl)-2-propenoate as light yellow oil. was added dropwise over 5 minutes at room temperature was added to the mixture dropwise over 20 minutes at room temperature this mixture was stirred for one hour at the same temperature the organic phase was separated After the resultant organic phase was washed with water a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate the solvent was distilled out under reduced pressure The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=9:1]

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 0.92 g of 60% sodium hydride was suspended in 30 mL of tetrahydrofuran, to which 5.0 mL of ethyl diethylphosphonoacetate was added dropwise over 5 minutes at room temperature, and this mixture was stirred for 30 minutes at 40° C. Then, after 3.40 g of 2-isobutoxybenzaldehyde dissolved in 20 mL of tetrahydrofuran was added to the mixture dropwise over 20 minutes at room temperature, this mixture was stirred for one hour at the same temperature. The reaction mixture was added to a mixture of ethyl acetate and water, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=9:1] to yield 4.30 g of ethyl (E)-3-(2-isobutoxyphenyl)-2-propenoate as light yellow oil. was added dropwise over 5 minutes at room temperature was added to the mixture dropwise over 20 minutes at room temperature this mixture was stirred for one hour at the same temperature the organic phase was separated After the resultant organic phase was washed with water a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate the solvent was distilled out under reduced pressure The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=9:1]

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 70.0 g of salicylaldehyde and 158.5 g of potassium carbonate were suspended in 700 mL of N,N-dimethylformamide, to which 68 mL of 3-chloro-2-methyl-1-propene was added dropwise over 30 minutes at 70° C., and this mixture was stirred for 30 minutes at the same temperature. Then, the reaction mixture was added to a mixture of ethyl acetate and water, and adjusted to pH 3 with 6M hydrochloric acid, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was dissolved in 350 mL of ethanol, to which 7.0 g of 5% palladium-carbon was added, and this mixture was stirred for 4 hours at 35° C. in a stream of hydrogen. After the reaction mixture was filtered through Celite, the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:toluene=2:1] to yield 92.4 g of 2-isobutoxybenzaldehyde as light yellow oil. was added dropwise over 30 minutes at 70° C. the organic phase was separated After the resultant organic phase was washed with water a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate the solvent was distilled out under reduced pressure The resultant residue was dissolved in 350 mL of ethanol, to which 7.0 g of 5% palladium-carbon was added this mixture was stirred for 4 hours at 35° C. in a stream of hydrogen After the reaction mixture was filtered through Celite the solvent was distilled out under reduced pressure The resultant residue was purified by silica gel column chromatography [eluent; hexane:toluene=2:1]

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In 200 ml of tetrahydrofuran are suspended 144 g of (methoxymethyl)triphenylphosphonium chloride and 43 g of diisopropylamine, to which is dropwise added 253 ml of a 1.6 mol/L solution of n-butyllithium in hexane at −50° C. over a period of one hour. The mixture thus obtained is stirred at ambient temperature for one hour. Then, a solution of 25 g of 2-isobutoxy-benzaldehyde in 100 ml of tetrahydrofuran is dropwise added to the reaction mixture obtained above at −50° C. over a period of one hour, and the mixture thus obtained is stirred at ambient temperature for one hour. The reaction mixture is added to a mixture of ethyl acetate and water, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue obtained above is mixed with 260 ml of 5% aqueous solution of sulfuric acid and 100 ml of dioxane, heated under reflux for 2 hours, cooled to ambient temperature and diluted with 500 ml of water. Ethyl acetate is added to the reaction mixture and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=95:5) to obtain 17.5 g of 2-(2-isobutoxyphenyl)ethanal as a colorless oily product. at −50° C. of one hour The mixture thus obtained obtained above at −50° C. over a period of one hour the mixture thus obtained is stirred at ambient temperature for one hour the organic layer is separated The organic layer is washed with water and saturated aqueous solution of sodium chloride successively dried over anhydrous magnesium sulfate the solvent is distilled off under reduced pressure The residue obtained heated under reflux for 2 hours cooled to ambient temperature the organic layer is separated The organic layer is washed with water and saturated aqueous solution of sodium chloride successively dried over anhydrous magnesium sulfate the solvent is distilled off under reduced pressure The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=95:5)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In 200 ml of tetrahydrofuran are suspended 144 g of (methoxymethyl)triphenylphosphonium chloride and 43 g of diisopropylamine, to which is dropwise added 253 ml of a 1.6 mol/L solution of n-butyllithium in hexane at −50° C. over a period of one hour. The mixture thus obtained is stirred at ambient temperature for one hour. Then, a solution of 25 g of 2-isobutoxy-benzaldehyde in 100 ml of tetrahydrofuran is dropwise added to the reaction mixture obtained above at −50° C. over a period of one hour, and the mixture thus obtained is stirred at ambient temperature for one hour. The reaction mixture is added to a mixture of ethyl acetate and water, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue obtained above is mixed with 260 ml of 5% aqueous solution of sulfuric acid and 100 ml of dioxane, heated under reflux for 2 hours, cooled to ambient temperature and diluted with 500 ml of water. Ethyl acetate is added to the reaction mixture and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=95:5) to obtain 17.5 g of 2-(2-isobutoxyphenyl)ethanal as a colorless oily product. at −50° C. of one hour The mixture thus obtained obtained above at −50° C. over a period of one hour the mixture thus obtained is stirred at ambient temperature for one hour the organic layer is separated The organic layer is washed with water and saturated aqueous solution of sodium chloride successively dried over anhydrous magnesium sulfate the solvent is distilled off under reduced pressure The residue obtained heated under reflux for 2 hours cooled to ambient temperature the organic layer is separated The organic layer is washed with water and saturated aqueous solution of sodium chloride successively dried over anhydrous magnesium sulfate the solvent is distilled off under reduced pressure The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=95:5)

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In 30 ml of tetrahydrofuran is suspended 0.92 g of 60% sodium hydride. After dropping 5.0 ml of ethyl diethylphosphonoacetate thereinto at ambient temperature over a period of 5 minutes, the mixture thus obtained is stirred at 40° C. for 30 minutes. Then, a solution of 3.40 g of 2-isobutoxybenzaldehyde in 20 ml of tetrahydrofuran is dropwise added at ambient temperature over a period of 20 minutes, and the mixture thus obtained is stirred for one hour. The reaction mixture is added to a mixture of ethyl acetate and water, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1) to obtain 4.30 g of ethyl 3-(2-isobutoxyphenyl)-2-propenoate as a light yellow oily product. the mixture thus obtained the mixture thus obtained is stirred for one hour the organic layer is separated The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride dried over anhydrous magnesium sulfate the solvent is distilled off under reduced pressure The residue thus obtained is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1)

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In 30 ml of tetrahydrofuran is suspended 0.92 g of 60% sodium hydride. After dropping 5.0 ml of ethyl diethylphosphonoacetate thereinto at ambient temperature over a period of 5 minutes, the mixture thus obtained is stirred at 40° C. for 30 minutes. Then, a solution of 3.40 g of 2-isobutoxybenzaldehyde in 20 ml of tetrahydrofuran is dropwise added at ambient temperature over a period of 20 minutes, and the mixture thus obtained is stirred for one hour. The reaction mixture is added to a mixture of ethyl acetate and water, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1) to obtain 4.30 g of ethyl 3-(2-isobutoxyphenyl)-2-propenoate as a light yellow oily product. the mixture thus obtained the mixture thus obtained is stirred for one hour the organic layer is separated The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride dried over anhydrous magnesium sulfate the solvent is distilled off under reduced pressure The residue thus obtained is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1)

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In 30 ml of tetrahydrofuran is suspended 0.92 g of 60% sodium hydride. After dropping 5.0 ml of ethyl diethylphosphonoacetate thereinto at ambient temperature over a period of 5 minutes, the mixture thus obtained is stirred at 40° C. for 30 minutes. Then, a solution of 3.40 g of 2-isobutoxybenzaldehyde in 20 ml of tetrahydrofuran is dropwise added at ambient temperature over a period of 20 minutes, and the mixture thus obtained is stirred for one hour. The reaction mixture is added to a mixture of ethyl acetate and water, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1) to obtain 4.30 g of ethyl 3-(2-isobutoxyphenyl)-2-propenoate as a light yellow oily product. the mixture thus obtained the mixture thus obtained is stirred for one hour the organic layer is separated The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride dried over anhydrous magnesium sulfate the solvent is distilled off under reduced pressure The residue thus obtained is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1)

反应条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In 700 ml of N,N-dimethylformamide are dissolved 70.0 g of salicylaldehyde and 158.5 g of potassium carbonate. After dropwise adding 67.9 ml of 3-chloro-2-methyl-1-propene at 70° C. over a period of 30 minutes, the mixture thus obtained is stirred at 70° C. for 30 minutes. The reaction mixture is added to a mixture of ethyl acetate and water, pH is adjusted to 3.0 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer thus obtained is successively washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is dissolved in 350 ml of ethanol, 7.0 g of 5% palladium-carbon is added, and the mixture is stirred at 35° C. for 4 hours in a stream of hydrogen. The reaction mixture is filtered with Celite, the solvent is distilled off from the filtrate under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; n-hexane:toluene=2:1) to obtain 92.4 g of 2-isobutoxybenzaldehyde as a light yellow oily product. the mixture thus obtained the organic layer is separated The organic layer thus obtained is successively washed with water and saturated aqueous solution of sodium chloride dried over anhydrous magnesium sulfate the solvent is distilled off under reduced pressure The residue thus obtained The reaction mixture is filtered with Celite the solvent is distilled off from the filtrate under reduced pressure The residue thus obtained is purified by silica gel column chromatography (eluent; n-hexane:toluene=2:1)