Sodium Chloride → 3-Methyl-6-dimethylaminopyridine-2-carbaldehyde

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Reaction Conditions

Reaction Steps

2.65 ml of a 1.6 M solution of n-butyllithium in hexane are introduced into a solution of 0.53 ml of N,N,N'-trimethylethylenediamine (4.24 mmol) and 10 ml of tetrahydrofuran cooled to -60° C. The solution is stirred for 15 minutes at -40° C. and then it is cooled to -70° C. and a solution of 0.50 g of 6-chloropyridine-2-carbaldehyde (3.53 mmol) and 4 ml of tetrahydrofuran is introduced dropwise. The orange-colored solution is stirred for 30 minutes at -70° C. and then 1.28 ml of tetramethylethylenediamine (8.48 mmol) are introduced and then after 10 minutes 5.30 ml of a 1.6M solution of n-butylithium in hexane are introduced. The brown solution is stirred for 2 hours at -78° C. and 1.50 ml of methyl iodide (25 mmol) are added dropwise. After stirring for one hour at -78° C. and then for 10 minutes at 20° C., the reaction mixture is poured into a saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The organic phase is washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and the solvent evaporated off. 0.23 g of the title product is recovered after purification by chromatography on a silica column (eluent: hexane/ethyl acetate; 95:5).

Provenance & Evidence