Hydrochloric Acid → 3-tert-Butyl-1-ethylcyclopenta-1,3-diene

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Reaction Steps

To a 200 ml three-neck flask equipped with a magnetic stirrer chip and a three-way cock, 50 ml of dehydrated diethyl ether and 59 ml (180 mmol) of diethyl ether solution of 3.0 M ethyl magnesium bromide were charged under a nitrogen atmosphere. In the ice-water bath, 21.4 g (155 mmol) of 3-tert-butylcyclopentenone was added dropwise over 1 hour. The resultant solution was stirred at room temperature for 16 hours, and then the reaction solution was poured into 100 ml of 3N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted twice with 50 ml of ether. The obtained organic layers were combined, washed once with a saturated aqueous solution of sodium hydrogencarbonate, twice with water, and once with saturated brine, and dried over magnesium sulfate and distilled off under reduced pressure to obtain 15.3 g of a pale yellowy transparent solution. The yield was 65%. Identification was done by 1H-NMR spectrum. The measurement results are shown as follows.

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