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

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Reaction Steps

N-(2-methoxy-3,4-methylenedioxybenzyl)aminoacetaldehyde diethylacetal (2) in an amount of 59.46 g (0.2 mol) and triethylamine in an amount of 28.45 ml (0.204 mol) were dissolved in 100 ml of methylene chloride, to which 38.88 g (0.204 mol) of p-toluenesulfonyl chloride in 80 ml of methylene chloride was added dropwise at 15°-30° C. over 25 minutes After stirring the mixture at room temperature for 30 minutes, 150 ml of water was added and the reaction mixture was stirred. The methylene chloride layer was separated from the aqueous layer and further washed with 100 ml of water. After drying the methylene chloride layer over anhydrous magnesium sulfate, the solvent was distilled off at reduced pressure to obtain 90.3 g of N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetal (3) as an oil. Yield: 100%. IR and NMR of the resultant product are listed below.

Provenance & Evidence