Triethylamine → 3-(Chloromethyl)-2-methylpyridine

Participants

Reaction Steps

To a solution of 3-hydroxymethy-2-methylpyridine (0.65 g, 5.3 mmol) in dry benzene (5 ml) was added triethylamine (1.0 ml, 7.4 mmol) followed by methanesulfonyl chloride (0.78 ml, 10.1 mmol) dropwise over 5 min. The heterogeneous dark gummy mixture was stirred at room temp. overnight. The reaction was filtered through Celite and washed with benzene (2×). The combined filtrates were washed with brine, dried (Na2SO4), and concentrated in vacuo to the crude product as a yellow oil which was used as is.

Provenance & Evidence