Methyl vinyl ketone → HCID 45085597, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cyclopropanecarbaldehyde (3.20 ml, 42.8 mmol) in ethanol (15.3 mL) was added triethylamine (11.9 mL, 86.0 mmol), but-3-en-2-one (3.54 mL, 42.8 mmol), and 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium bromide (2.16 g, 8.56 mmol). The reaction mixture was heated at 85° C. for 18.5 h. The reaction was then concentrated and the resulting residue was extracted with ethyl acetate (3×50 mL). The organic layer was dried (sodium sulfate), filtered and concentrated to an orange residue which was purified on silica gel on an automated system (ISCO 120 g, 20 mL/min) using 0 to 75% ethyl acetate in hexanes over 60 minutes. The product, 1-cyclopropylpentane-1,4-dione, was isolated as a yellow oil (2.21 g, 15.8 mmol, 37% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 2.86 (t, 2H), 2.72 (t, 2H), 2.19 (s, 3H), 1.90-1.99 (m, 1H), 1.01 (m, 2H), 0.88 (m, 2H).

Provenance & Evidence