Pyridine → HCID 54082424, compound

Participants

Reaction Steps

0.078 Mole of 2-hydroxy-2-(bicyclo[3.1.0]hex-2-yl)acetonitrile is dissolved in 200 ml. of anhydrous pyridine under nitrogen, and cooled to -50° C. 0.0942 Mole of thionyl chloride is added dropwise and the mixture allowed to warm to room temperature and then recooled to 0° C. Excess thionyl chloride is then decomposed by the addition of 2 ml. of water. The pyridine is removed by evaporation under vacuum and the resulting residue dissolved in 300 ml. of ethyl acetate. The ethyl acetate solution is then washed twice with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate is evaporated to dryness, under vacuum, and the resulting residue is chromatographed with silica gel eluting with 10% ethyl acetate-90%, vol., hexane, affording 2-(cyanomethylene)bicyclo[3.1.0]hexane.

Provenance & Evidence