3-Methyl-2-cyclopenten-1-one → 1-Tert-butyl-3-methylcyclopenta-1,3-diene

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Reaction Steps

To a solution obtained by adding 350 ml of dehydrated diethyl ether to 450 ml (0.90 mol) of a tert-butylmagnesium chloride/diethyl ether solution (concentration: 2.0 mol/liter), a solution of 43.7 g (0.45 mmol) of 3-methylcyclopentenone in 150 ml of dehydrated diethyl ether was dropwise added in a nitrogen atmosphere at 0° C. with ice cooling, followed by stirring at room temperature for 15 hours. To the reaction solution, a solution of 80.0 g (1.50 mol) of ammonium chloride in 350 ml of water was dropwise added at 0° C. with ice cooling. To the resulting solution, 2500 ml of water was added, followed by stirring. Then, the organic phase was separated and washed with water. To the organic phase, 82 ml of a 10% hydrochloric acid aqueous solution was added at 0° C. with ice cooling, followed by stirring at room temperature for 6 hours. The organic phase was separated from the reaction solution, washed with water, a saturated sodium hydrogencarbonate aqueous solution, water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. The drying agent was filtered, and from the filtrate the solvent was distilled off to obtain a liquid. The liquid was subjected to vacuum distillation (45-47° C./10 mmHg) to obtain 14.6 g of a light yellow liquid. The analyzed values are given below.

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