HCID 19966028, compound → HCID 19966031, compound

Participants

Reaction Steps

3.08 g (47.1 mmol) of zinc powder and then 0.32 ml of acetic acid were added to 16 ml of a methanolic solution containing 847 mg (2.36 mmol) of 2-t-butyl-5-(5-cycloheptyl-3-oxopentyl)-1-nitrobenzene (prepared as described in Preparation 6), in an ice bath. The mixture was then stirred for 1 hour. At the end of this time, a further 0.32 ml of acetic acid was added, and the mixture was stirred for a further 1 hour. The reaction mixture was then filtered using a Celite filter aid. The insoluble material was washed with ethyl acetate. The filtrate and the washings were combined, condensed to about 10 ml by evaporation under reduced pressure, and diluted with ethyl acetate to distribute the desired compound between the organic solvent and water. In order to remove the insoluble material, the solution was filtered again using a Celite filter aid and the insoluble material was washed again with ethyl acetate. The organic layer was combined with the washings and washed with a saturated aqueous solution of sodium hydrogen carbonate and then with water. The solvent was then removed by distillation under reduced pressure, to obtain 789 mg (a quantitative yield) of the title compound as an oily substance.

Provenance & Evidence