Acetone → 1,6,6-Trimethyl-3-tert-butyl-fulvene

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Reaction Steps

In a nitrogen atmosphere, dried acetone (55.2 g, 950.4 mmol) was added dropwise to a solution of 1-tert-butyl-3-methylcyclopentadiene (13.0 g, 95.6 mmol) in dried methanol (130 ml), and subsequently pyrrolidine (68.0 g, 956.1 mmol) was added thereto dropwise. During the dropwise addition, the temperature was kept at 0° C. by ice cooling. The mixture was stirred at room temperature for 4 days. The resultant reaction liquid was diluted with diethyl ether (400 ml), and water (400 ml) was added. The organic phase was separated, then washed with a 0.5 N aqueous hydrochloric acid solution (150 ml×4), water (200 ml×3) and a saturated saline solution (150 ml), 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 (70-80° C./0.1 mm Hg) to give 10.5 g of a yellow liquid. The analytical data are given below.

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