Sodium Hydroxide → 4-Methyl-5-(oxiran-2-yl)pyridine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-ethenyl-4-methylpyridine-3-carbonitrile (3.00 g, 20.8 mmol) in 30 mL of ButOH and 60 mL of water was added NBS (4.6 g, 26 mmol) portionwise. The mixture was stirred at 40° C. for 2.5 hour then cooled down to 10° C. NaOH solution (2.5 g in 70 mL of water, 62.4 mmol) was added dropwise and stirred for 15 minutes. The reaction mixture was extracted with EtOAc twice and condensed. The residue was purified by column chromatography (petrol ether: EtOAc=20:1) to afford 4-methyl-5-(oxiran-2-yl)pyridine-3-carbonitrile.

Provenance & Evidence