Water → HCID 58310972, compound

Participants

Reaction Steps

A solution of 3-fluorobenzaldehyde (2.005 ml, 18.33 mmol) in DMF (5 ml) was added dropwise over the course of 0.5 hours to a mixture of sodium cyanide (0.450 g, 9.18 mmol) in DMF (20 ml) at 35° C. Stirring was then continued for 1.5 hours at 35° C. A solution of (E)-4-phenylbut-3-en-2-one (2.0 g, 13.68 mmol) in DMF (5 ml) was then slowly added dropwise over the course of 0.5 hours at 35° C. Stirring was continued for 3.5 hours at the same temperature. The reaction mixture was treated with twice its volume of water and extracted with DCM. The combined extracts were washed with water and brine, dried with Na2SO4, filtered and concentrated to give a liquid, purified by chromatography on silica gel using an automated Biotage system (EtOAc/Hex, 0-50%) to give 1-(3-fluorophenyl)-2-phenylpentane-1,4-dione (2.1 g, 7.77 mmol, 56.8% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.75-7.73 (m, 1H), 7.64-7.61 (m, 1H), 7.37-7.12 (m, 7H), 5.03 (dd, 1H), 3.61 (dd, 1H), 2.76 (dd, 1H), 2.19 (s, 3H).

Provenance & Evidence