methyl 2-(2-formylphenoxy)acetate

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:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2. Approximately 509 g of the starting compound, salicylaldehyde (1) was introduced into a 4-liter Erlenmeyer flask with powdered potassium carbonate (569 g), dimethylformnamide (1,000 ml), and methyl chloroacetate (478 g) and mechanically stirred at 65° C. for about 24 hours. The stirring was stopped and the reaction mixture cooled to 25° C. The mixture was poured into cold water (0° C.) while stirring vigorously. An oil separated that suddenly solidified. Stirring was continued for 30 minutes and the solid isolated by filtration. The product was washed with water (2×1,000 ml) and pressed dry. The product can also be dried in vacuo at 25° C. A small sample (approx. 2 g) was purified by distillation. The boiling range of the pure product is 124-128° C. at 2 mm Hg and has a melting temperature range of about 50.2-50.6° C. the reaction mixture cooled to 25° C while stirring vigorously An oil separated Stirring was continued for 30 minutes the solid isolated by filtration The product was washed with water (2×1,000 ml) pressed dry The product can also be dried in vacuo at 25° C A small sample (approx. 2 g) was purified by distillation is 124-128° C. at 2 mm Hg a melting temperature range of about 50.2-50.6° C.

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:111.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The crude product 2 was placed into a 5-liter 3-necked round-bottomed flask equipped with a mechanical stirrer and a water trap. Toluene (1,900 ml) was added and the solution heated at reflux temperature (111° C.) until all water had been removed. Diazabicyclounde-7-ene (DBU) (65 g) was then added and the mixture was stirred at 111° C., without the water trap, until the starting material was no longer present, i.e., was not detectable by TLC monitoring. Most of the solvent (90%) was then distilled off. The residue was cooled to 25° C., and ethyl acetate (1,000 ml) was added. The mixture was transferred to a separatory funnel and the organic solution washed with 2N HCl (2×1,000 ml), then with water (1,000 ml). Drying was done over magnesium sulfate. The crude product (326.56 g) was a dark oil and was used directly in the next step. A small sample was purified for the purpose of structure elucidation: the crude material (2 g) was dissolved in ethyl ether and washed with 1N KOH. Drying was done over magnesium sulfate, the material was filtered, and the solvent evaporated. The oily residue was crystallized from isopropanol. The melting range is 53.8°-54° C. equipped with a mechanical stirrer and a water trap the solution heated had been removed Diazabicyclounde-7-ene (DBU) (65 g) was then added Most of the solvent (90%) was then distilled off The residue was cooled to 25° C. ethyl acetate (1,000 ml) was added The mixture was transferred to a separatory funnel the organic solution washed with 2N HCl (2×1,000 ml) Drying A small sample was purified for the purpose of structure elucidation the crude material (2 g) was dissolved in ethyl ether washed with 1N KOH Drying the material was filtered the solvent evaporated The oily residue was crystallized from isopropanol

反応条件: temp:111.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The crude product 2 was placed into a 5-liter 3-necked round-bottomed flask equipped with a mechanical stirrer and a water trap. Toluene (1,900 ml) was added and the solution heated at reflux temperature (111° C.) until all water had been removed. Diazabicyclounde-7-ene (DBU) (65 g) was then added and the mixture was stirred at 111° C., without the water trap, until the starting material was no longer present, i.e., was not detectable by TLC monitoring. Most of the solvent (90%) was then distilled off. The residue was cooled to 25° C., and ethyl acetate (1,000 ml) was added. The mixture was transferred to a separatory funnel and the organic solution washed with 2N HCl (2×1,000 ml), then with water (1,000 ml). Drying was done over magnesium sulfate. The crude product (326.56 g) was a dark oil and was used directly in the next step. A small sample was purified for the purpose of structure elucidation: the crude material (2 g) was dissolved in ethyl ether and washed with 1N KOH. Drying was done over magnesium sulfate, the material was filtered, and the solvent evaporated. The oily residue was crystallized from isopropanol. The melting range is 53.8°-54° C. equipped with a mechanical stirrer and a water trap the solution heated had been removed Diazabicyclounde-7-ene (DBU) (65 g) was then added Most of the solvent (90%) was then distilled off The residue was cooled to 25° C. ethyl acetate (1,000 ml) was added The mixture was transferred to a separatory funnel the organic solution washed with 2N HCl (2×1,000 ml) Drying A small sample was purified for the purpose of structure elucidation the crude material (2 g) was dissolved in ethyl ether washed with 1N KOH Drying the material was filtered the solvent evaporated The oily residue was crystallized from isopropanol

反応条件: temp:111.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The crude product 2 was placed into a 5-liter 3-necked round-bottomed flask equipped with a mechanical stirrer and a water trap. Toluene (1,900 ml) was added and the solution heated at reflux temperature (111° C.) until all water had been removed. Diazabicyclounde-7-ene (DBU) (65 g) was then added and the mixture was stirred at 111° C., without the water trap, until the starting material was no longer present, i.e., was not detectable by TLC monitoring. Most of the solvent (90%) was then distilled off. The residue was cooled to 25° C., and ethyl acetate (1,000 ml) was added. The mixture was transferred to a separatory funnel and the organic solution washed with 2N HCl (2×1,000 ml), then with water (1,000 ml). Drying was done over magnesium sulfate. The crude product (326.56 g) was a dark oil and was used directly in the next step. A small sample was purified for the purpose of structure elucidation: the crude material (2 g) was dissolved in ethyl ether and washed with 1N KOH. Drying was done over magnesium sulfate, the material was filtered, and the solvent evaporated. The oily residue was crystallized from isopropanol. The melting range is 53.8°-54° C. equipped with a mechanical stirrer and a water trap the solution heated had been removed Diazabicyclounde-7-ene (DBU) (65 g) was then added Most of the solvent (90%) was then distilled off The residue was cooled to 25° C. ethyl acetate (1,000 ml) was added The mixture was transferred to a separatory funnel the organic solution washed with 2N HCl (2×1,000 ml) Drying A small sample was purified for the purpose of structure elucidation the crude material (2 g) was dissolved in ethyl ether washed with 1N KOH Drying the material was filtered the solvent evaporated The oily residue was crystallized from isopropanol

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Approximately 509 g of the starting compound, salicylaldehyde (1) was introduced into a 4-liter Erlenmeyer flask with powdered potassium carbonate (569 g), dimethylformamide (1,000 ml), and methyl chloroacetate (478 g) and mechanically stirred at 65° C. for about 24 hours. The stirring was stopped and the reaction mixture cooled to 25° C. The mixture was poured into cold water (0° C.) while stirring vigorously. An oil separated that suddenly solidified. Stirring was continued for 30 minutes and the solid isolated by filtration. The product was washed with water (2×1,000 ml) and pressed dry. The product can also be dried in vacuo at 25° C. A small sample (approx. 2 g) was purified by distillation. The boiling range of the pure product is 124°-128° C. at 2 mm Hg and has a melting temperature range of about 50.2°-50.6° C. the reaction mixture cooled to 25° C while stirring vigorously An oil separated Stirring was continued for 30 minutes the solid isolated by filtration The product was washed with water (2×1,000 ml) pressed dry The product can also be dried in vacuo at 25° C A small sample (approx. 2 g) was purified by distillation is 124°-128° C. at 2 mm Hg a melting temperature range of about 50.2°-50.6° C.

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Approximately 509 g of the starting compound, salicylaldehyde (1) was introduced into a 4-liter Erlenmeyer flask with powdered potassium carbonate (569 g), dimethylformamide (1,000 ml), and methyl chloroacetate (478 g) and mechanically stirred at 65° C. for about 24 hours. The stirring was stopped and the reaction mixture cooled to 25° C. The mixture was poured into cold water (0° C.) while stirring vigorously. An oil separated that suddenly solidified. Stirring was continued for 30 minutes and the solid isolated by filtration. The product was washed with water (2×1,000 ml) and pressed dry. The product can also be dried in vacuo at 25° C. A small sample (approx. 2 g) was purified by distillation. The boiling range of the pure product is 124°-128° C. at 2 mm Hg and has a melting temperature range of about 50.2°-50.6° C. the reaction mixture cooled to 25° C while stirring vigorously An oil separated Stirring was continued for 30 minutes the solid isolated by filtration The product was washed with water (2×1,000 ml) pressed dry The product can also be dried in vacuo at 25° C A small sample (approx. 2 g) was purified by distillation is 124°-128° C. at 2 mm Hg a melting temperature range of about 50.2°-50.6° C.

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

実験手順: A mixture of ethyl trimethylacetopyruvate (0.40 g, 2 mmol), 4-thiophene-3-ylaniline (0.35 g, 2 mmol), 2-(methoxycarbonylmethyloxy)benzaldehyde (0.39, 2 mmol), acetic acid (0.057 mL, 1 mmol) and dioxane (4 mL) was heated at reflux overnight. After the reaction was completed, saturated sodium bicarbonate solution and brine were poured into the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulphate, and then concentrated in vacuo. The resulting residue was purified on a silica gel column chromatography (methanol/chloroform), and the aimed compound was triturated with ethyl acetate and diisopropyl ether to give 4-(2,2-dimethylpropionyl)-3-hydroxy-5-(2-methoxycarbonylmethyloxyphenyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one (0.42 g, yield: 41%) as pale brown solid. was heated at reflux overnight the resulting mixture was extracted with ethyl acetate The extract was dried over anhydrous sodium sulphate concentrated in vacuo The resulting residue was purified on a silica gel column chromatography (methanol/chloroform) the aimed compound was triturated with ethyl acetate and diisopropyl ether

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2. Approximately 509 g of the starting compound, salicylaldehyde (1) was introduced into a 4-liter Eriemeyer flask with powdered potassium carbonate (569 g), dimethylformamide (1,000 ml), and methyl chloroacetate (478 g) and mechanically stirred at 65° C. for about 24 hours. The stirring was stopped and the reaction mixture cooled to 25° C. The mixture was poured into cold water (0° C.) while stirring vigorously. An oil separated that suddenly solidified. Stirring was continued for 30 minutes and the solid isolated by filtration. The product was washed with water (2×1,000 ml) and pressed dry. The product can also be dried in vacuo at 25° C. A small sample (approx. 2 g) was purified by distillation. The boiling range of the pure product is 124°-128° C. at 2 mm Hg and has a melting temperature range of about 50.2°-50.6° C. the reaction mixture cooled to 25° C while stirring vigorously An oil separated Stirring was continued for 30 minutes the solid isolated by filtration The product was washed with water (2×1,000 ml) pressed dry The product can also be dried in vacuo at 25° C A small sample (approx. 2 g) was purified by distillation is 124°-128° C. at 2 mm Hg a melting temperature range of about 50.2°-50.6° C.

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2. Approximately 509 g of the starting compound, salicylaldehyde (1) was introduced into a 4-liter Erlenmeyer flask with powdered potassium carbonate (569 g), dimethylformamide (1,000 ml), and methyl chloroacetate (478 g) and mechanically stirred at 65° C. for about 24 hours. The stirring was stopped and the reaction mixture cooled to 25° C. The mixture was poured into cold water (0° C.) while stirring vigorously. An oil separated that suddenly solidified. Stirring was continued for 30 minutes and the solid isolated by filtration. The product was washed with water (2×1,000 ml) and pressed dry. The product can also be dried in vacuo at 25° C. A small sample (approx. 2 g) was purified by distillation. The boiling range of the pure product is 124°-128° C. at 2 mm Hg and has a melting temperature range of about 50.2°-50.6° C. the reaction mixture cooled to 25° C while stirring vigorously An oil separated Stirring was continued for 30 minutes the solid isolated by filtration The product was washed with water (2×1,000 ml) pressed dry The product can also be dried in vacuo at 25° C A small sample (approx. 2 g) was purified by distillation is 124°-128° C. at 2 mm Hg a melting temperature range of about 50.2°-50.6° C.