Dimethyl Sulfoxide → 2-Methyl-5-(oxiran-2-yl)pyridine

Participants

Reaction Conditions

Reaction Steps

DMSO is added to NaH 60% dispersion in oil (1-1.8 equiv.) and heated to 65° C. for 1 h. THF is added to the mixture at the same temperature and heated for another 10 min. After 10 min., the reaction mixture is cooled to 0° C. Trimethylsulfonium iodide (1-1.2 equiv.) is added and the contents are stirred for 10 min. A solution of 6-methylnicotinaldehyde (1 equiv.) in THF is added dropwise. After complete addition, the reaction mixture is stirred at RT for 2 h, and monitored by LCMS. The reaction mixture is poured in ice water, extracted in diethyl ether, dried over sodium sulfate and concentrated at 25° C. to get crude product 2-methyl-5-(oxiran-2-yl)pyridine.

Provenance & Evidence