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

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Reaction Steps

In a nitrogen atmosphere, dried diethyl ether (350 ml) was added to a tert-butylmagnesium chloride/diethyl ether solution (450 ml, 0.90 mol, a 2.0 mol/l solution). A solution of 3-methylcyclopentenone (43.7 g, 0.45 mmol) in dried diethyl ether (150 ml) was added dropwise to the solution while keeping the temperature at 0° C. by ice cooling. The mixture was stirred at room temperature for 15 hours. To the reaction solution, a solution of ammonium chloride (80.0 g, 1.50 mol) in water (350 ml) was added dropwise while keeping the temperature at 0° C. with ice cooling. Water (2500 ml) was added to the resultant solution, and the mixture was stirred. The organic phase was separated and washed with water. Thereafter, a 10% aqueous hydrochloric acid solution (82 ml) was added to the organic phase while the temperature was kept at 0° C. with ice cooling. The mixture was stirred at room temperature for 6 hours. The organic phase of the resultant reaction liquid was separated, then washed with water, a saturated aqueous sodium hydrogen carbonate solution, water and a saturated saline solution, and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled away from the filtrate, resulting in a liquid. The liquid was distilled under reduced pressure (45-47° C./10 mm Hg) to give 14.6 g of a light yellow liquid. The analytical data are given below.

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