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

Participants

Reaction Conditions

Reaction Steps

44 mg (1.1 mmol) of 60% oil dispersion of sodium hydride was washed twice with 2 ml of dry hexane to eliminate oil. 2 ml of dry N,N-dimethylformamide, 335 mg (1 mmol) of N-(2-methoxy-3,4-methylenedioxybenzyl)-p-toluenesulfonamide (1) and 0.18 ml (1.1 mmol) of bromoacetaldehyde diethylacetal (purity 95%) were added in order. The resulting mixture was stirred at 100° C. for 10 hours. On cooling, to this 5 ml of water was added and the reaction mixture was extracted with 8 ml and then 2 ml of methylene chloride successively. The liquid extract was washed with 5 ml of water, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under vacuum and the residue was purified by silica gel column chromatography (eluate: ethylacetate/n-hexane=1/4) to obtain 358 mg of N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetal (2) as an oil. Yield 79%.

Provenance & Evidence