Sodium methanethiolate → 2-Ethyl-5-(methylsulfanyl)pyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 5-bromo-2-ethylpyridine (see part (i)) (3.0 g, 16.2 mmol) in dry DMF (4.5 ml) was treated with sodium methanethiolate (1.8 g, 24.3 mmol) and the suspension heated at 100° C. for 3 hours. The cooled mixture was diluted with diethyl ether (200 ml), washed with water (4×100 ml), then dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography on silica by elution with dichloromethane. The appropriate fractions were combined and evaporated under reduced pressure. The resulting oil was distilled under reduced pressure (60 mm) at an oven temperature of 150° C. using a Kugelrohr (trade mark) apparatus to give the title compound, (1.4 g).

Provenance & Evidence