Acetic Acid → 4-[(Pyrrolidin-1-yl)methyl]benzaldehyde

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Reaction Steps

To a solution of 4-(dimethoxymethyl)benzaldehyde (25.0 g, 120 mmol), pyrrolidine (10.0 ml, 120 mmol), acetic acid (6.87 ml, 120 mmol) and anhydrous sodium sulfate (34.1 g, 240 mmol) in dichloromethane (300 ml) was added sodium triacetoxyborohydride (38.2 g, 180 mmol), and the mixture was stirred for 3 days. Potassium carbonate was added to the reaction mixture, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate). 1N Hydrochloric acid (300 ml) was added to the obtained oil, and the mixture was washed with diethyl ether after 2 hrs. The aqueous layer was basified with potassium carbonate, and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate) to give the title compound (22.7 g).

Provenance & Evidence