Water → HCID 178458874, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.7 g (15.0 mmol) of potassium t-butoxide in 20 mL of methyl sulfoxide at room temperature was treated with 2.0 g (7.7 mmol) of 2-propionyl-3-hydroxy-5-((4-hydroxyphenyl)-phenyl)cyclohex-2-en-1-one. After 15 minutes of stirring, 2.0 g (11 mmol) of 3-fluorophenylmethylsulfone was added thereto and the solution was heated, under nitrogen, at 120° C. for 7 hours. The mixture was cooled to room temperature, poured into 100 mL of cold water and washed with 30 mL of diether ether and acidified with 1N HCl to pH 4 and extracted thrice with 20 mL portions of methylene chloride. The combined extracts were dried over MgSO4, filtered and passed through a short column of silica gel. Evaporation of the solvent afforded the above named product as a light green oil. The product was recovered in a yield of 2.5 g (78 percent of theoretical). A small sample was crystallized to reveal the product as a white solid which melted at 109.5°-113.5° C. 1H NMR (CDCl3) δ1.17 (t, J=7 Hz, 3H, --CH2CH3), 2.63-3.65 (m includes s at 3.03 for CH3SO2 --, 10H), 6.97-7.78 (m, 8H, aromaties), 18.1 (s, 1H, enol H).

Provenance & Evidence