HCID 68380040, compound → HCID 68380044, compound

Participants

Reaction Steps

A mixture of 3-[2-(benzyloxy)-5-fluorophenyl]-2,2-dichlorocyclobutanone (C18) (1.4 g, 4.14 mmol) and zinc dust (1.08 g, 16.5 mmol) in acetic acid (25 mL) was stirred at room temperature for 2 hours and then at 100° C. for 1.25 hours. The mixture was filtered through Celite, and the filtrate was washed with water (50 mL) and saturated aqueous sodium chloride solution (50 mL), dried over magnesium sulfate and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 30% ethyl acetate in heptanes) afforded the title compound as a colorless oil. Yield: 674 mg, 2.49 mmol, 60%. LCMS m/z 179.4 [M−(C7H7)]. 1H NMR (400 MHz, CDCl3) δ 3.22-3.31 (m, 2H), 3.36-3.46 (m, 2H), 3.75-3.85 (m, 1H), 5.08 (s, 2H), 6.87-6.95 (m, 2H), 6.99 (dd, J=9.2, 2.7 Hz, 1H), 7.33-7.44 (m, 5H).

Provenance & Evidence