1,10-Phenanthroline → 2-[(1-Hydroxy-1-methylpropyl)]-1,10-phenanthroline

Participants

Reaction Conditions

Reaction Steps

An embodiment of the process comprises mixing a stirred solution of 1,10-phenanthroline in tetrahydrofuran (THF) with a solution of the lanthanideII, samarium diiodide, in THF at a temperature of about 25° C. To the mixed solutions is added a solution of the ketone, methyl ethyl ketone, and the reaction mixture is stirred at about 25° C. for about 12 hours. The reaction is then quenched by the addition of a saturated aqueous solution of ammonium chloride and the mixture extracted with methylene chloride. The extract is washed with brine, dried and concentrated in vacao. The concentrate of product is purified by flash chromatography using alumina and ethyl acetate-hexanes as a gradient to provide racemic 2-[(1-hydroxy-1-methylpropyl)]-1,10-phenanthroline. (Formula 1, R=H, R1=ethyl, R2=methyl) This embodiment is depicted in the following reaction scheme wherein MEK is methyl ethyl ketone.

Provenance & Evidence