{4-[2-(Tetrahydropyran-2-yloxy)ethoxy]benzofur-7-yl}acetic acid ethyl ester → {4-[2-(Tetrahydropyran-2-yloxy)ethoxy]benzofur-7-yl}acetic acid

Participants

Reaction Steps

Add to a cooled solution (0° C.) of {4-[2-(tetrahydropyran-2-yloxy)ethoxy]-benzofur-7-yl}acetic acid ethyl ester (1.363 g, 3.912 mmol) in dimethylformamide (20 ml) 2M aqueous sodium hydroxide (10 ml), and stir the mixture for 1½ hours at room temperature. Dilute the mixture with ethyl acetate and extract with water. Dilute with methylene chloride (50 ml) and neutralize using 0.1M aqueous hydrochloric acid (100 ml). Separate the layers are separated and extract the water layer with methylene chloride. Combine the methylene chloride layers, dry over sodium sulfate, filter, and concentrate to obtain 0.920 g (68%) of the title compound as an oil. Mass spectrum: electrospray (m/z) 319 (M−1).

Provenance & Evidence