Triethylamine → Rac-2,2-dimethylpropionic acid 2-(4-bromo-2,6-dimethylphenyl)-3-oxo-4-(tetrahydropyran-4-ylmethyl)cyclopent-1-enyl ester

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Reaction Steps

To a solution of rac-2-(4-bromo-2,6-dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione (1.0 g, 2.6 mmol) in dichloromethane (20 ml) is added triethylamine (1.09 ml, 7.8 mmol) then pivaloyl chloride (1.10 ml, 7.8 mmol), and the resulting solution is stirred at room temperature for 4 hours. The reaction mixture is diluted with dichloromethane (100 ml), washed with distilled water (50 ml×3), and the organic fractions are combined, dried over sodium sulphate, filtered and the filtrate concentrated in vacuo to afford rac-2,2-dimethylpropionic acid 2-(4-bromo-2,6-dimethylphenyl)-3-oxo-4-(tetrahydropyran-4-ylmethyl)cyclopent-1-enyl ester. This material is used directly in the next step without further purification.

Provenance & Evidence