Toluene → (6-Acetoxymethyl-benzofuran-3-yl)-acetic acid ethyl ester

Beteiligte Stoffe

Reaktionsschritte

To a solution of acetic acid 3-oxo-2,3-dihydro-benzofuran-6-ylmethyl ester (1.50 g, 7.27 mmol) in toluene (260 mL) was added (caboxymethylene)triphenyl phosphorane (12.67 g, 36.37 mmol) and the mixture was refluxed for 24 h. The reaction mixture was allowed to cool to room temperature and concentrated. The residue was purified by column chromatography (ethylacetate:hexane; 5:95) to give the (6-acetoxymethyl-benzofuran-3-yl)-acetic acid ethyl ester as a off white solid (1.15 g, 57%). 1H NMR (CDCl3, 400 MHz) 1.27 (t, J=7.1 Hz, 3H), 2.11 (s, 3H), 3.69 (s, 2H), 4.19 (q, J=7.1 Hz, 2H), 5.21 (s, 2H), 7.26 (d, J=8.0 Hz, 1H), 7.50 (s, 1H), 7.56 (d, J=8.0 Hz, 1H), 7.65 (s, 1H), 13C NMR (CDCl3, 100 MHz) 14.2, 21.0, 29.9, 61.1, 66.4, 111.6, 113.1, 119.8, 123.1, 127.7, 132.6, 143.5, 155.2, 170.5, 170.9.

Herkunft & Nachweise