Potassium Cyanide → 4-[3-[6-(3-Bromo-5-cyanomethyl-phenoxy)-hexyl]-2-(2-ethoxy carbonylethyl)-phenoxy]-butyric acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[3-[6-(3-bromo-5-methanesulfonyloxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.51 g, 3.74 mmol) in DMF (40 mL), KCN (292 mg, 4.48 mmol) was added and stirred a 60° C. overnight. The reaction was diluted with EtOAc (250 mL) washed with water (100 mL×2), brine (50 mL), dried with Na2SO4. Concentration under reduced pressure provided an oil. Flash column chromatography (30% EtOAc/Hex) provided a light yellow oil (1.19 g, 53% yield). 1H NMR (CDCl3): δ 7.08 (t, 1H), 7.04 (s, 1H), 6.99 (s, 1H), 6.79 (s, 1H), 6.77 (d, 1H), 6.68 (d, 1H), 4.17-4.06 (m, 4H), 4.01-3.91 (m, 4H), 3.68 (s, 2H), 2.97 (dd, 2H), 2.63 (dd, 2H), 2.56-2.46 (m, 4H), 2.17-0.89 (m, 16H).

Provenance & Evidence