Water → HCID 178458875, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.7 g (15.0 mmol) of potassium t-butoxide in 15 mL of methyl sulfoxide at room temperature was treated with 2.0 g (11 mmol) of 2-propionyl-3-hydroxy-5-((4-hydroxyphenyl)-phenyl)cyclohex-2-en-1-one. After 20 minutes of stirring, 2.0 g (11 mmol) of (4-fluorophenyl)methyl sulfone was added thereto and the solution was heated, under nitrogen, at 100° C. for 2.5 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 solid residue which was recrystallized from absolute alcohol. The product was recovered in a yield of 2.4 g (75 percent of theoretical) and melted at 157-158° C. 1H NMR (CDCl3) δ1.18 (t, J=7 Hz, 3H, --CH2CH3), 2.70-3.58 (m includes s at 3.03 for CH3SO 2 --, 10H), 7.00-7.38 (m, 6H, aromatics), 7.89 (d, J=9 Hz, 2H, aromatics), 18.17 (s, 1H, enol H).

Provenance & Evidence