Hydrochloric Acid → HCID 86619564, compound

Participants

Reaction Steps

A 300 ml three neck flask equipped with a magnetic stirrer and a three-way cock was charged with 5.11 g (23.9 mmol) (GC purity: 75%) of 1-ethyl-3-tert-butylcyclopentadiene and 150 ml of THF under nitrogen atmosphere. A 1.56M n-butyllithium hexane solution 16 ml (25.2 mmol) was added dropwise thereto on a dry ice/methanol bath, and then the solution was stirred at room temperature for 20 hours. 1,3-Dimethyl-2-imidazolidinone 3.1 ml (28.8 mmol) was added to the reaction solution obtained, and subsequently 5.3 g (28.8 mmol) of benzophenone was added thereto and stirred for 48 hours under refluxing. The reaction solution was poured into 100 ml of 2N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted twice with 50 ml of hexane. It was combined with the previous organic layer and washed with a saturated sodium hydrogen carbonate aqueous solution, water and a saturated sodium chloride aqueous solution. The organic layer was dried on magnesium sulfate, and then the solvent was removed by distillation. Thereafter, the residue was purified by column chromatography to obtain 4.2 g of an orange solid matter. The yield was 56%. The product was identified by means of a 1H-NMR spectrum. The measurement results thereof are shown below.

Provenance & Evidence