Water → N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetal

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Reaction Steps

59.46 g (0.2 mol) of N-(2-methoxy-3,4-methylenedioxybenzyl)aminoacetaldehyde diethylacetal (1) and 28.45 ml (0.204 mol) of triethylamine were dissolved in 100 ml of methylene chloride, to which 38.8 g (0.204 mol) of p-toluenesulfonyl chloride in 80 ml of methylene chloride was added dropwise at 15°-30° C. for 25 minutes. After stirring at room temperature for 30 minutes, 150 ml of water was added to the reaction mixture, which was stirred followed by liquid separation and then being washed with 100 ml of water. After drying the methylene chloride layer over anhydrous magnesium sulfate, the solvent was distilled off under vacuum to obtain 90.3 g of N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetal (2) as an oil. Yield 100%. IR and NMR spectra of the resultant product are listed below. ##STR26##

Provenance & Evidence