[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O-:16])(=O)[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[NH2:10].S([O-])([O-])(=O)=O.[Na+].[Na+].CCOCC.[CH2:29]1[CH2:33][O:32][CH2:31][CH2:30]1>>[CH3:33][O:32][CH2:31][CH2:30][CH2:29][NH:10][C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[CH2:7][OH:16]To a suspension of 0.96 g (25.3 mmol) of lithium aluminium hydride in 40 ml of dry THF was dropwise added a solution of 4.0 g (16.9 mmol) of methyl N.(3.methoxypropanoyl) anthranilate in 10 ml of dry THF under chilling with ice for a period of 15 min. The mixture was then heated under reflux for 1 hr. To the resulting mixture, a saturated aqueous sodium sulfate was added under chilling with ice to decompose the excess lithium aluminium hydride. After the addition of 40 ml of ether, insolubles were removed by sellaite filtration. The organic portion was collected and dried over anhydrous sodium sulfate, then the solvent was distilled off under reduced pressure to leave 3.1 g of the desired compound as a pale yellow oil. (Yield: 94.0 %)
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