3-Pyridinecarboxaldehyde → 3-(Oxiran-2-yl)pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.59 g of 3-pyridinecarboxaldehyde and 62 mg of tetra-n-butylammonium bromide in 60 mL CH2Cl2 at room temperature is added a solution of 10.0 g of trimethylsulfonium methylsulfate in 15 mL H2O. The resulting solution is set stirring and cooled to 0° C. Aqueous NaOH (50% w/w; 40 mL) is added in portions while stirring and the mixture subsequently refluxed for 1 h. After cooling to room temperature, the mixture is filtered and the filtrate extracted with CH2Cl2. The combined extracts are dried over MgSO4, filtered, and concentrated to yield a red oil, which is subjected to Kugelrohr distillation under high vacuum at 150° C. to yield 838 mg of the title compound as a clear, light yellow oil.

Provenance & Evidence