Hydrochloric Acid → HCID 86619564, compound

Participants

Reaction Steps

To a 300-ml three-necked flask equipped with a magnetic stirring bar and a three-way cock was charged with 5.11 g (23.9 mmol) of 1-ethyl-3-tert-butylcyclopentadiene (GC purity 75%) and 150 ml of THF under nitrogen atmosphere. To the solution was added, slowly and dropwise, 16 ml of a hexane solution of n-butyllithium (1.56 M: 25.2 mmol) in a dry ice/methanol bath, and the mixture was stirred at room temperature for 20 hours. To the resultant reaction liquid were added 3.1 ml (28.8 mmol) of 1,3-dimethyl-2-imidazolidinone and then 5.3 g (28.8 mmol) of benzophenone, and the solution was stirred under reflux for 48 hours. The reaction solution was poured into 100 ml of 2N hydrochloric acid. The organic layer was separated and the aqueous layer was subjected to extraction with 50 ml of hexane twice. The combined organic layer was washed with saturated sodium hydrogen carbonate aqueous solution, water, and saturated brine. After drying over magnesium sulfate, the solvent was distilled off. The residue was purified by column chromatography to obtain 4.2 g of an orange solid. The yield was 56%. The identification was carried out by 1H-NMR spectrum. The measurement results are shown below.

Provenance & Evidence