反应详情

To the suspension of [3-(1H-indol-4-yl)phenyl]-acetic acid methyl ester (3.72 g, 14 mmol) in t-BuOH: ethanol: acetic acid (93 mL: 56 mL: 67.2 mL) was added pyridinium tribromide (14.14 g, 44 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added acetic acid (60 mL). Water (2 mL) and zinc dust (14 g, excess) was added to the reaction mixture portionwise. After stirring at rt for one hour, any unreacted zinc was filtered off and most of the solvent was removed under reduced pressure. The residue was diluted with diluted with water (380 mL), extracted with ethyl acetate, washed with 0.5 N HCl (2×), 10% Na2CO3, (2×), brine (2×), water (1×), dried over Na2SO4, concentrated and triturated with ether to give [3-(2-oxo-2,3-dihydro-1H-indol-4-yl)phenyl]-acetic acid methyl ester.

1. stirringAfter stirring at rt for one hour
2. filtrationany unreacted zinc was filtered off and most of the solvent
3. customwas removed under reduced pressure
4. additionThe residue was diluted
5. additionwith diluted with water (380 mL)
6. extractionextracted with ethyl acetate
7. washwashed with 0.5 N HCl (2×), 10% Na2CO3, (2×), brine (2×), water (1×)
8. dry with materialdried over Na2SO4
9. concentrationconcentrated
10. customtriturated with ether