Water → 2-[(2-Bromophenyl)methyl]-6-[(phenylmethoxy)methyl]-cyclohexanone

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Reaction Steps

To a solution of the ketone of Example 113 in benzene is added pyrrolidine (4 equivalents). The mixture is heated to reflux for 24 hours removing the water formed by use of a Dean-Stark type apparatus. The reaction mixture is concentrated in vacuo. The organics are dissolved in dioxane followed by addition of 2-bromobenzyl bromide (1.5 equivalents). The mixture is heated to reflux for 6 hours. Water is added and the refluxing continued for 3 hours. The solution is concentrated in vacuo to dryness. The remaining organics are partitioned between ether and water. The ether layer is dried (MgSO4), concentrated in vacuo, then chromatographed to give the title compound.

Provenance & Evidence