Triethylamine → Aniline, 4-ethyl-N-methyl-

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Reaction Steps

4-Ethylaniline (2.4 g, 20 mmol) was dissolved in dichloromethane (150 ml), and triethylamine (8.4 ml, 60 mmol) and ethyl chloroformate (5.8 ml, 60 mmol) were added to the solution to stir the mixture for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was dissolved in diethyl ether (20 ml). The solution was added dropwise to a suspension (20 ml) of lithium aluminum hydride (2.4 g, 63.2 mmol) in diethyl ether under cooling with ice water in a nitrogen atmosphere. The mixture was stirred for 1 hours as it was, and for 2 hours at room temperature. The solvent was distilled off under reduced pressure, and tetrahydrofuran (20 ml) was added to the residue. The resultant mixture was heated under reflux for 1 hour and 40 minutes. Ice and then water were gradually added to the reaction mixture. After potassium sulfate was additionally added, the mixture was extracted with ethyl acetate. The extract was additionally extracted with 1N hydrochloric acid. After the resultant extract was basified with a 4N aqueous solution of sodium hydroxide, it was extracted 3 times in total with ethyl acetate (twice) and diethyl ether (once), and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography on silica gel (hexane:ethyl acetate=20:1) to obtain 1.8 g of the title compound (oil).

Provenance & Evidence