Water → HCID 136144744, compound

Participants

Reaction Steps

A solution of 0.70 g (1.8 mmol) of 2-propionyl-3-hydroxy-5-(3-(2-fluoro-4-(methylsulfonyl)phenoxy)-phenyl)cyclohex-2-en-1-one in 5 mL of methylene chloride and 10 mL of absolute ethanol, at room temperature was treated with 0.22 g (2.3 mmol) of ethoxyamine hydrochloride and 0.19 g (2.3 mmol) of anhydrous sodium acetate. After stirring under a nitrogen atmosphere for 16 hours, the mixture was poured into 100 mL of water and extracted twice with 30 mL portions of methylene chloride. The combined extracts were dried over MgSO4, filtered and the solvent evaporated off leaving the product as a dark yellow oil. Purification via flash chromatography (silica gel, methylene chloride/hexane) the above named product as a light amber oil in a yield of 0.6 g (77 percent of theoretical). 1H NMR (CDCl3): δ1.2-1.5 (m, 6H, both --CH2CH3 's), 2.58 (s, 3H, --SCH3), 2.50-3.65 (m, 7H), 4.25 (q, J=7 Hz, 2H, --OCH2), 6.8-7.5 (m, 7H, aromatics), 14.9 (broad s, 1H, enol H) (Compound 5).

Provenance & Evidence