Isopropyl iodide → HCID 56850328, compound

Participants

Reaction Steps

Diisopropyl 1,3-adamantanedicarboxylate is prepared by way of the following procedure. A 50 mL round bottom flask equipped with magnetic stir bar is charged with 1,3-admantanedicarboxylic acid (2.76 g, 12.3 mmol), 2-iodopropane (3.07 mL, 30.8 mmol) and 1,8-diazabicycloundec-7-ene (4.60 mL, 30.8 mmol) in 25 mL acetonitrile. The mixture is heated to reflux overnight and cooled to room temperature. The reaction is diluted with 100 mL of ethyl acetate and washed with saturated NH4Cl/1N HCl, water, saturated sodium bicarbonate, and then brine. The organic layer is dried over sodium sulfate. After filtration, the filtrate is concentrated, and the residue is dried in vacuo. The crude product is further purified by distillation in vacuo to yield the product as a white liquid.

Provenance & Evidence