methyl 2-(2-hydroxyphenyl)-2-oxoacetate

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: 10.4 g (0.0533 mol) of methyl 2-hydroxyphenylglyoxylate (HPLC: 92.4%, log p=1.87) from process step 2 and 7.4 g (0.089 mol) of 0-methylhydroxylamine hydrochloride in 150 ml of methanol are boiled under reflux for three hours. The reaction mixture is poured into water, the product is extracted with diethyl ether, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 8.2 g of crude product which, according to HPLC, contains 17.2% methyl E-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=1.48 and 65.4% methyl Z-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=2.38. under reflux for three hours the product is extracted with diethyl ether the organic phase is dried over sodium sulphate the solvent is distilled off under reduced pressure

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

実験手順: 27 g of acetyl chloride (0.344 mol) are added dropwise to a mixture of 245 ml of methanol and 245 ml of acetone. 20 g (0.123 mol) of benzofuran-2,3-dione 2-oxime are dissolved in this mixture and the mixture is subsequently heated under reflux for 1 hour. The solvent is distilled off under reduced pressure, the residue is poured into water, the product is extracted with diethyl ether, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 20.8 g of crude product which, according to HPLC, contains 92.4% methyl 2-hydroxyphenylglyoxylate of log p=1.87. the mixture is subsequently heated under reflux for 1 hour The solvent is distilled off under reduced pressure the residue is poured into water the product is extracted with diethyl ether the organic phase is dried over sodium sulphate the solvent is distilled off under reduced pressure

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

実験手順: 10.4 g (0.0533 mol) of methyl 2-hydroxyphenylglyoxylate (HPLC: 92.4%, log p=1.87) from process step 2 and 7.4 g (0.089 mol) of 0-methylhydroxylamine hydrochloride in 150 ml of methanol are boiled under reflux for three hours. The reaction mixture is poured into water, the product is extracted with diethyl ether, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 8.2 g of crude product which, according to HPLC, contains 17.2% methyl E-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=1.48 and 65.4% methyl Z-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=2.38. under reflux for three hours the product is extracted with diethyl ether the organic phase is dried over sodium sulphate the solvent is distilled off under reduced pressure

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

実験手順: 3.3 g (0.016 mol) of methyl 2-hydroxyphenylglyoxylate (HPLC: 88%, log p=1.87) (Example VI-1a) and 1.3 g (0.019 mol) of hydroxylamine hydrochloride in 50 ml of methanol are heated under reflux for one hour. The reaction mixture is poured into water, acidified with 2N hydrochloric acid and extracted with diethyl ether, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 2.4 g of crude product which, according to HPLC, contains 17.1% of methyl E-2-(2-hydroxyphenyl)-2-hydroxyimino-acetate of log p=0.95 and 68.9% of methyl Z-2-(2-hydroxyphenyl)-2-hydroxyimino-acetate of log p=1.68. under reflux for one hour extracted with diethyl ether the organic phase is dried over sodium sulphate the solvent is distilled off under reduced pressure

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

実験手順: 3.3 g (0.016 mol) of methyl 2-hydroxyphenylglyoxylate (HPLC: 88%, log p=1.87) (Example VI-1a) and 1.3 g (0.019 mol) of hydroxylamine hydrochloride in 50 ml of methanol are heated under reflux for one hour. The reaction mixture is poured into water, acidified with 2N hydrochloric acid and extracted with diethyl ether, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 2.4 g of crude product which, according to HPLC, contains 17.1% of methyl E-2-(2-hydroxyphenyl)-2-hydroxyimino-acetate of log p=0.95 and 68.9% of methyl Z-2-(2-hydroxyphenyl)-2-hydroxyimino-acetate of log p=1.68. under reflux for one hour extracted with diethyl ether the organic phase is dried over sodium sulphate the solvent is distilled off under reduced pressure

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

実験手順: 6.38 g of acetyl chloride (0.081 mol) are added dropwise to a mixture of 65 ml of methanol and 65 ml of acetone. 5.2 g (0.032 mol) of benzofuran-2,3-dione 2-oxime are dissolved in this mixture, and the mixture is subsequently heated under reflux for 1 hour. The solvent is distilled off under reduced pressure, the residue is poured into water, the product is extracted with diethyl ether, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 5.2 g of crude product which is chromatographed over silica gel using a mixture of 7 parts n-hexane and 3 parts acetone. This gives 3.8 g of a product which, according to HPLC, contains 88% of methyl 2-hydroxyphenylglyoxylate of log p=1.87. the mixture is subsequently heated under reflux for 1 hour The solvent is distilled off under reduced pressure the residue is poured into water the product is extracted with diethyl ether the organic phase is dried over sodium sulphate the solvent is distilled off under reduced pressure This gives 5.2 g of crude product which is chromatographed over silica gel using a mixture of 7 parts n-hexane and 3 parts acetone

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: 10.4 g (0.0533 mol) of methyl 2-hydroxyphenylglyoxylate (HPLC: 92.4%, log p=1.87) from process step 2 and 7.4 g (0.089 mol) of 0-methylhydroxylamine hydrochloride in 150 ml of methanol are boiled under reflux for three hours. The reaction mixture is poured into water, the product is extracted with diethyl ether, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 8.2 g of crude product which, according to HPLC, contains 17.2% methyl E-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=1.48 and 65.4% methyl Z-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=2.38. under reflux for three hours the product is extracted with diethyl ether the organic phase is dried over sodium sulphate the solvent is distilled off under reduced pressure

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

実験手順: 27 g of acetyl chloride (0.344 mol) are added dropwise to a mixture of 245 ml of methanol and 245 ml of acetone. 20 g (0.123 mol) of benzofuran-2,3-dione 2-oxime are dissolved in this mixture and the mixture is subsequently heated under reflux for 1 hour. The solvent is distilled off under reduced pressure, the residue is poured into water, the product is extracted with diethyl ether, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 20.8 g of crude product which, according to HPLC, contains 92.4% methyl 2-hydroxyphenylglyoxylate of log p=1.87. the mixture is subsequently heated under reflux for 1 hour The solvent is distilled off under reduced pressure the residue is poured into water the product is extracted with diethyl ether the organic phase is dried over sodium sulphate the solvent is distilled off under reduced pressure

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

実験手順: 3.3 g (0.016 mol) of methyl 2-hydroxyphenylglyoxylate (HPLC: 88%, log p=1.87) (Example VI-1a) and 1.3 g (0.019 mol) of hydroxylamine hydrochloride in 50 ml of methanol are heated under reflux for one hour. The reaction mixture is poured into water, acidified with 2N hydrochloric acid and extracted with diethyl ether, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 2.4 g of crude product which, according to HPLC, contains 17.1% of methyl E-2-(2-hydroxyphenyl)-2-hydroxyimino-acetate of log p=0.95 and 68.9% of methyl Z-2-(2-hydroxyphenyl)-2-hydroxyimino-acetate of log p=1.68. under reflux for one hour extracted with diethyl ether the organic phase is dried over sodium sulphate the solvent is distilled off under reduced pressure

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

実験手順: 6.38 g of acetyl chloride (0.081 mol) are added dropwise to a mixture of 65 ml of methanol and 65 ml of acetone. 5.2 g (0.032 mol) of benzofuran-2,3-dione 2-oxime are dissolved in this mixture, and the mixture is subsequently heated under reflux for 1 hour. The solvent is distilled off under reduced pressure, the residue is poured into water, the product is extracted with diethyl ether, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 5.2 g of crude product which is chromatographed over silica gel using a mixture of 7 parts n-hexane and 3 parts acetone. This gives 3.8 g of a product which, according to HPLC, contains 88% of methyl 2-hydroxyphenylglyoxylate of log p=1.87. the mixture is subsequently heated under reflux for 1 hour The solvent is distilled off under reduced pressure the residue is poured into water the product is extracted with diethyl ether the organic phase is dried over sodium sulphate the solvent is distilled off under reduced pressure This gives 5.2 g of crude product which is chromatographed over silica gel using a mixture of 7 parts n-hexane and 3 parts acetone