7-苄氧基吲哚-2-甲酸乙酯

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: A solution of 7-benzyloxyindole-2-carboxylic acid ethyl ester in 600 ml of tetrahydrofuran and 200 ml of methanol is combined with 500 ml of 2N sodium hydroxide solution and stirred for 3 hours at room temperature. The reaction mixture is then acidified under ice cooling with 10% hydrochloric acid and extracted twice with ethyl acetate. The combined organic phases are dried, treated with active carbon, and concentrated. The residue is recrystallized from toluene, thus producing 35 g of 7-benzyloxyindole-2-carboxylic acid, mp 166°-168° C. extracted twice with ethyl acetate The combined organic phases are dried treated with active carbon concentrated The residue is recrystallized from toluene

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

实验步骤: One gram of 10% palladium catalyst on active carbon is added to a solution of 22.2 g of 7-benzyloxyindole-2-carboxylic acid ethyl ester in 500 ml of ethanol and the mixture is hydrogenated for 1 hour with shaking under normal pressure. The reaction solution is then filtered and the filtrate evaporated to dryness under vacuum. The residue is recrystallized from ethanol, yielding 13.3 g of 7-hydroxyindole-2-carboxylic acid ethyl ester, mp 197°-199° C. The reaction solution is then filtered the filtrate evaporated to dryness under vacuum The residue is recrystallized from ethanol

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

实验步骤: Under agitation, 26.3 g of oxalic acid diethyl ester and, 15 minutes later, a solution of 21.9 g of 3-benzyloxy-2-nitrotoluene in 30 ml of diethyl ether are added dropwise to a suspension of 9 g of potassium ethanolate in 200 ml of diethyl ether. The reaction mixture is heated for 20 hours under reflux; the thus-separated potassium salt of 3-benzyloxy-2-nitrophenylpyruvic acid ethyl ester is vacuum-filtered and washed with diethyl ether. The salt is then dissolved in a mixture of 200 ml of ethanol and 200 ml of concentrated acetic acid, the solution is combined with 50 g of powdered iron and heated under reflux for 90 minutes. The reaction mixture is allowed to cool, poured into 1 liter of ice water, filtered over kieselguhr, and the kieselguhr washed with diethyl ether. The organic phase is separated and the aqueous phase is extracted three times with diethyl ether. The combined organic phases are washed with saturated sodium carbonate solution, dried, and concentrated under vacuum. The residue is recrystallized from ethanol, thus obtaining 9.6 g of 7-benzyloxyindole-2-carboxylic acid ethyl ester, mp 82°-83° C. The reaction mixture is heated for 20 hours under reflux the thus-separated potassium salt of 3-benzyloxy-2-nitrophenylpyruvic acid ethyl ester is vacuum-filtered washed with diethyl ether The salt is then dissolved in a mixture of 200 ml of ethanol and 200 ml of concentrated acetic acid heated under reflux for 90 minutes to cool poured into 1 liter of ice water filtered over kieselguhr the kieselguhr washed with diethyl ether The organic phase is separated the aqueous phase is extracted three times with diethyl ether The combined organic phases are washed with saturated sodium carbonate solution dried concentrated under vacuum The residue is recrystallized from ethanol