反应详情

A mixture of 1-(4-hydroxy-phenyl)-3-phenyl-propan-1-one from Example K (6.9 g, 30.5 mmol), and cesium carbonate (19.9 g, 61 mmol) was dissolved in dioxane (300 mL). This mixture was heated to reflux for 1 hour then treated with iodoethanol (2.85 mL, 36.5 mmol) and refluxed overnight; the reaction mixture was cooled and concentrated. The product was partitioned between EtOAc and 1N HCl. The organic layer was dried (MgSO4) and concentrated to dryness. Purification by silica gel chromatography, eluting with EtOAc:hexane (30:70 to 50:50) gave the title compound, m.p. 41°-43° C. 1H NMR (CDCl3) δ 1.96 (t, 1 H), 3.02 (t, 2 H), 3.22 (t, 2 H), 3.95 (m, 2 H), 4.10 (m, 2 H), 6.92 (d, 2 H), 7.15-7.28 (m, 5 H), 7.90 (d, 2 H).

1. temperatureThis mixture was heated
2. temperatureto reflux for 1 hour
3. temperaturerefluxed overnight
4. temperaturethe reaction mixture was cooled
5. concentrationconcentrated
6. customThe product was partitioned between EtOAc and 1N HCl
7. dry with materialThe organic layer was dried (MgSO4)
8. concentrationconcentrated to dryness
9. customPurification by silica gel chromatography
10. washeluting with EtOAc:hexane (30:70 to 50:50)