Potassium Carbonate → 2-Acetyl-2-[2-(tert-butoxycarbonyl)ethyl]cyclohexanone

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-acetylcyclohexanone (100 g, 0.71 mol), potassium carbonate (118.3 g, 0.85 mol) and benzyltriethylammonium chloride (3.18 g, 0.014 mol) in toluene (280 ml), was added, in one portion, tert-butyl acrylate (137.1 g, 155.2 ml, 1.07 mol) at room temperature. The suspension was stirred at 40° C. for 18 hours, diluted with distilled water (1 L) and toluene (500 ml), and the layers separated. The aqueous layer was extracted with toluene (3×500 ml), the combined toluene extracts dried over magnesium sulphate, filtered and concentrated under reduced pressure to give a brown oil, (197.8 g). Rf. 0.41 (silica, hexane/ethyl acetate, 3:1). The crude product was used without further purification.

Provenance & Evidence