2-香豆素

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:; See reaction.notes.procedure_details.

实验步骤: 0.40 g of the compound (7.4) are dissolved together with 0.175 g of 4-hydroxy-methyl-pyranone (Fluka) in 40 mL of phosphate buffer (0.2M, pH=5) at room temperature, and 20.0 mg of laccase (Trametes versicolor (Fluka)) are added. For better solubility, 1 mL of ethanol is also added. The mixture is stirred in an open vessel until the starting materials can no longer be detected (about 2 days). The mixture is concentrated and the residue is taken up in methanol and centrifuged. The desired product (211 mg) is obtained in the form of a brownish-beige solid. The product can be purified further by reprecipitation from ether/methanol mixtures. 20.0 mg of laccase (Trametes versicolor (Fluka)) are added (about 2 days) The mixture is concentrated

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

实验步骤: A mixture of 0.4 mol of coumaranone and 0.48 mol of methyl (triphenylphosphoranylidene)acetate in 1 liter of p-xylene is maintained at reflux for 18 h. After cooling to room temperature, the solvent is evaporated off, the residue is taken up in 1 liter of ether, the precipitate is filtered off and washed with ether, the filtrate is concentrated and the expected product is obtained after chromatography on silica (eluent: CH2Cl2). is maintained at reflux for 18 h the solvent is evaporated off the precipitate is filtered off washed with ether the filtrate is concentrated

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

实验步骤: A solution of 2-coumaranone (5.0 g, 37 mmol) and methyl(triphenylphosphoranylideneacetate) (13.5 g. 40 mmol) in toluene (70 mL) was heated to reflux for 25 hours. More toluene was added (10 mL), and after a further 5 hours, more methyl(triphenylphosphoranylideneacetate) (0.5 g, 1.5 mmol). After another 19 hours, a further 1.0 g (3.0 mmol) was added, and after a further 21 hours, the solvent was removed in vacuo. Column chromatography (heptane:ethyl acetate 4:1) gave the product as a brown oil, 28 mmol, 75%. to reflux for 25 hours After another 19 hours a further 1.0 g (3.0 mmol) was added after a further 21 hours the solvent was removed in vacuo

反应条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of benzofuran-2(3H)-one (20 g) dissolved in DMF (250 mL) was treated with iodomethane (33.4 mL) at 0° C. before adding potassium carbonate (134 g) portionwise over a period of 10 minutes under nitrogen. The resulting suspension was stirred at 25° C. for 3 days. The mixture was filtered and the solids washed with ethyl acetate. The filtrate was diluted with 2M hydrochloric acid, extracted with ethyl acetate. The organic was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified (SiO2 chromatography eluting with 30% dichloromethane in iso-hexane). Pure fractions were evaporated to dryness to afford the subtitle compound (19.70 g). The mixture was filtered the solids washed with ethyl acetate The filtrate was diluted with 2M hydrochloric acid extracted with ethyl acetate The organic was dried (MgSO4) filtered evaporated to afford crude product The crude product was purified (SiO2 chromatography eluting with 30% dichloromethane in iso-hexane) Pure fractions were evaporated to dryness

反应条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Sodium (18.9 parts) was dissolved in absolute ethanol (380 parts) with stirring and was cooled to 20° C. and benzofuranone (100 parts) and 3-methoxybenzaldehyde were added. The reaction mixture was stirred under reflux for 15 minutes and cooled to 20° C. over 1 hour. The reaction mixture was poured into water (900 parts) and the ethanol was removed by evaporation under reduced pressure. Hydrochloric acid was added to the solution until acid and the aqueous phase was decanted to leave a red gum. The gum was dissolved in hot acetic acid (300 parts) and the solution was cooled to 20° C. and a solid was precipitated. The solid was isolated by filtration, washed with ethanol (74 OP) and dried to give 2-(3-methoxyphenyl)-1,3-indandione (55.8 parts) m.pt. 142°-144° C. The reaction mixture was stirred under reflux for 15 minutes cooled to 20° C. over 1 hour the ethanol was removed by evaporation under reduced pressure Hydrochloric acid was added to the solution until acid the aqueous phase was decanted to leave a red gum the solution was cooled to 20° C. a solid was precipitated The solid was isolated by filtration washed with ethanol (74 OP) dried

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:; See reaction.notes.procedure_details.

实验步骤: To a solution of 262.3 g (1.00 mol) of 5,7-di-tert-butyl-3-hydroxy-3H-benzofuran-2-one (compound (201), Table 2, Example la) in 500 ml (4.05 mol) of o-xylene are added 40 g of Fulcat 22B and the mixture is refluxed for 1.5 hours on a water separator. The Fulcat 22B catalyst is then removed by filtration and excess p-xylene is removed by distillation on a vacuum rotary evaporator. Crystallisation of the residue from 500 ml of methanol yields 244 g (69%) of 3-(3,4-dimethylphenyl)-5,7-di-tert-butyl)-3H-benzofuran-2-one, m.p. 130-132° C. (compound (103), Table 1), which additionally contains c. 1.3% of the structural isomer [3-(2,3-dimethylphenyl)-5,7-di-tert-butyl-3H-benzofuran-2-one, compound (103A)]. The mother liquor yields a further 42.4 g of product which, according to GC-MS analysis, consists of 12.3% of the compound (103) and 87.7% of the isomeric compound (103A). The Fulcat 22B catalyst is then removed by filtration and excess p-xylene is removed by distillation on a vacuum rotary evaporator Crystallisation of the residue from 500 ml of methanol

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

实验步骤: To a solution of 262.3 g (1.00 mol) of 5,7-di-tert-butyl-3-hydroxy-3H-benzofuran-2-one (compound (201), Table 2, Example la) in 500 ml (4.05 mol) of o-xylene are added 40 g of Fulcat 22B and the mixture is refluxed for 1.5 hours on a water separator. The Fulcat 22B catalyst is then removed by filtration and excess p-xylene is removed by distillation on a vacuum rotary evaporator. Crystallisation of the residue from 500 ml of methanol yields 244 g (69%) of 3-(3,4-dimethylphenyl)-5,7-di-tert-butyl)-3H-benzofuran-2-one, m.p. 130-132° C. (compound (103), Table 1), which additionally contains c. 1.3% of the structural isomer [3-(2,3-dimethylphenyl)-5,7-di-tert-butyl-3H-benzofuran-2-one, compound (103A)]. The mother liquor yields a further 42.4 g of product which, according to GC-MS analysis, consists of 12.3% of the compound (103) and 87.7% of the isomeric compound (103A). The Fulcat 22B catalyst is then removed by filtration and excess p-xylene is removed by distillation on a vacuum rotary evaporator Crystallisation of the residue from 500 ml of methanol

反应条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Sodium (18.9 parts) was dissolved in absolute ethanol (380 parts) with stirring and was cooled to 20° C. and benzofuranone (100 parts) and 3-methoxybenzaldehyde were added. The reaction mixture was stirred under reflu for 15 minutes and cooled to 20° C. over 1 hour. The reaction mixture was poured into water (900 parts) and the ethanol was removed by evaporation under reduced pressure. Hydrochloric acid was added to the solution until acid and the aqueous phase was decanted to leave a red gum. The gum was dissolved in hot acetic acid (300 parts) and the solution was cooled to 20° C. and a solid was precipitated. The solid was isolated by filtration, washed with ethanol (74 OP) and dried to give 2-(3-methoxyphenyl)-1,3-indandione (55.8 parts) m.pt. 142°-144° C. The reaction mixture was stirred under reflu for 15 minutes cooled to 20° C. over 1 hour the ethanol was removed by evaporation under reduced pressure Hydrochloric acid was added to the solution until acid the aqueous phase was decanted to leave a red gum the solution was cooled to 20° C. a solid was precipitated The solid was isolated by filtration washed with ethanol (74 OP) dried