Water → HCID 60147146, compound

Participants

Reaction Steps

A solution of 5-{2-[4′-(2-benzylbenzofuran-3-yl)-biphen-4-yl]-2-oxoethyl}-2,2-dimethyl-[1,3]dioxane-4,6-dione (200 mg, 0.37 mmol) in THF/DMF (5:1; 6 mL) was added dropwise to a stirred suspension of sodium hydride (95%, 10.2 mg, 0.40 mmol) in anhydrous THF (5 mL) at room temperature. The clear solution was stirred at room temperature for 30 mins and then a solution of benzyl bromide (76 mg, 0.44 mmol) in THF (5 mL) was added dropwise, followed by the addition of tetra-n-butylammonium iodide (5 mg) as a solid. The reaction mixture was warmed to 60° C. for 4 hrs (TLC control), cooled to room temperature and then water (10 mL) was added cautiously. The reaction mixture was extracted with diethyl ether (3×15 mL). The combined extract was washed with water (2×10 mL), brine (3×10 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by trituration and filtration from MeOH afforded the title compound as a pale yellow solid (210 mg). 1H-NMR (CDCl3, 300 MHz): δ 8.12 (2H, d, J=8 Hz, Ar-H), 7.88 (4H, d, J=6 Hz, Ar-H), 7.53-7.69 (4H, m, Ar-H), 7.26 (1H, m, Ar-H), 7.14 (11H, m, Ar-H), 4.26 (2H, s, PhCH2), 4.16 (2H, CH2CO), 3.38 (2H, s, PhCH2), 1.98 (3H, s, Me), 0.78 (3H, s, Me).

Provenance & Evidence