Methyl Acrylate → Methyl 2,2-diMethyl-3-oxocyclobutanecarboxylate

Participants

Reaction Steps

The suspension of methyl acrylate (1.3 equiv.), 1-chloro-N,N,2-trimethylprop-1-en-1-amine (1.0 equiv.), and zinc trifluoromethanesulfonate (0.25 equiv.) was stirred to blend its contents for 15 min at room temperature under N2. Then the mixture was sonicated (100 W) at 36-39° C. for 24 h. A mixture of THF:H2O=10:1 was added to the mixture and sonicated. The mixture was concentrated and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by silica gel chromatography (petroleum ether; petroleum ether:ethyl acetate=50:1, 10:1) to afford the title compound methyl 2,2-dimethyl-3-oxocyclobutanecarboxylate (29% yield) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ (ppm) 3.73 (s, 3H), 3.51 (dd, J=7.6 Hz, 18.4 Hz, 1H), 3.07 (q, J=9.2 Hz, 18 Hz 1H), 2.94 (t, J=7.2 Hz, 8.8 Hz, 1H), 1.29 (s, 3H), 1.09 (s, 3H).

Provenance & Evidence