Triethylamine → 3-Ethoxy-4,4-dipropyl-2-cyclobuten-1-one

Participants

Reaction Steps

The title compound was prepared using a modification of the method of Wasserman, H. H. et al, [J. Org. Chem, 38, 1451–1455, (1973)]; triethylamine (29 ml) was added dropwise at room temperature to a well-stirred solution of di-n-propylacetyl chloride (13.9 g, 85.8 mmol) and ethyl ethynylether (15 g, 40% solution in hexanes, 85.7 mmol) in toluene (120 ml. The reaction was warmed to 60° and stirred for 48 h prior to cooling and filtration. The filtrate was concentrated in vacuo and the residual oil chromatographed (SiO2; hexanes 80:EtOAc 20) to give the title compound as a brown oil (11.2 g, 57.1 mmol, 67%). δH (CDCl3, 300K) 5.02 (1H, s), 4.32 (2H, q, J 7.1 Hz), 1.69–1.61 (4H, m), 1.45–1.40 (4H, m), 1.02 (6H, t, J 7.3 Hz). m/z (ES+, 70V) 197.1 (MH+).

Provenance & Evidence