Water → 3-Methyl-2-(phenylmethylthio)-pyridine

Participants

Reaction Steps

A suspension of 4.8 g (100 mmole) of sodium hydride in 50 mls of dimethylformamide was cooled to 0° and 11.6 ml (100 mmole) of benzyl mercaptan was added dropwise at 0°. After addition was complete, the reaction mixture was allowed to warm to 25° and stirred at this temperature for 1 hour. The reaction mixture was then re-cooled to 0° and 10.0 g (91 mmole) of 2-fluoro-3-methyl pyridine was added dropwise. The mixture was allowed to warm to 25° and stirred at this temperature for 18 hours. The mixture was poured into 100 mls of water and extracted twice with ethyl ether and ethylacetate. The combined organic extracts were washed with a saturated solution of sodium bicarbonate and dried over sodium sulfate. Concentration gave 24 g of a yellow oil. Flash chromatography in a 10% ethyl ether/hexanes mixture gave 6.3 g clear oil.

Provenance & Evidence