Hydrochloric Acid → HCID 66672730, compound

Participants

Reaction Steps

To a solution of 1-{3-methyl-4-[(phenylmethyl)oxy]phenyl}ethanone (0.81 g, 3.4 mmol) in tetrahydrofuran (11 mL) was added sodium hydride (0.27 g, 6.7 mmol) followed by methyl 2-{[2-(methyloxy)ethyl]oxy}benzoate (0.70 g, 3.4 mmol, Harkin, S. H.; Wells, N. S., GB Patent 2250511, 1992) and the resultant mixture was heated in a 60° C. oil bath for 12 h. The solution was allowed to cool to room temperature and was diluted with water then 1M aqueous hydrochloric acid. The mixture was extracted (3× ethyl acetate) and the combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Column chromatography (silica gel, 5:1 hexanes/ethyl acetate) gave 0.24 g (17%) of 1-(2-{[2-(methyloxy)ethyl]oxy}phenyl)-3-{3-methyl-4-[(phenylmethyl)oxy]phenyl}propane-1,3-dione as a colorless oil. 1H NMR (400 MHz, CDCl3): 8.01 (dd, 1H), 7.89 (m, 2H), 7.34-7.45 (m, 7H), 7.08 (t, 1H), 6.97 (d, 1H), 6.92 (d, 1H), 5.17 (s, 2H), 4.24 (m, 2H), 3.85 (m, 2H), 3.42 (s, 3H), 2.34 (s, 3H).

Provenance & Evidence