Water → HCID 86585669, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of diethyl glutaconate (10.0 g. 53.7 mmol), 3-chloroiodobenzene (11.5 g, 48.2 mmol), sodium acetate (4.40 g, 53.7 mmol) and palladium acetate (1.1 g, 4.9 mmol) in DMF (30 mL) was heated to 100° C., stirred for 21 hours, cooled to room temperature, poured into water, filtered, and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel 8:1 hexanes/ethyl acetate to provide 2.88 g (20%) of the desired product. MS (DCI/NH3) m/z 297 (M+H)−; 1H NMR (CDCl3) δ 7.43 (m, 2H), 7.32 (m, 3H), 6.26 (s, 2H), 4. 19 (m, 4H), 1.21 (t, 3H), 1.31 (t, 3H).

Provenance & Evidence