Methyl vinyl ketone → 1-Cyclohexylpentane-1,4-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of cyclopentanecarbaldehyde (2.00 g, 20.38 mmol) in ethanol (7.2 mL) was added triethylamine (5.68 mL, 40.8 mmol), but-3-en-2-one (1.69 mL, 26.7 mmol), and 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium bromide (1.03 g, 4.08 mmol). The reaction mixture was heated at 85° C. for 72 hours after which it was concentrated. The resulting residue was extracted with ethyl acetate (3×50 mL) and the organic layers were dried (sodium sulfate), filtered and concentrated to an orange residue which was used in the next step without further purification. The crude product, 1-cyclohexylpentane-1,4-dione (3.68 g, 21.9 mmol) was isolated as an orange oil. 1H NMR (400 MHz, CDCl3) δ (ppm): 2.91 (m, 1H), 2.68-2.78 (m, 4H), 2.19 (s, 3H), 1.70-1.87 (m, 4H), 1.54-1.69 (m, 4H).

Provenance & Evidence