Cesium carbonate → 2-[4-Benzyloxy-2-(hydroxy-phenyl-methyl)-phenoxy]-2-methyl-propionic Acid Ethyl Ester

Temperature

55 °C

4-Benzyloxy-2-(hydroxy-phenyl-methyl)-phenol (690 mg, 2.25 mmol) and Cs2CO3 (734 mg, 2.25 mmol) in DMF (7 mL) was treated with ethyl bromoisobutyrate (0.66 mL, 4.5 mmol) and heated at 55° C. for 16 h. Additional bromo ester (0.40 mL, 1.23 mmol) and CS2CO3 (400 mg, 1.23 mmol) were added and the reaction mixture was heated for 40 h. The mixture was cooled and partitioned between EtOAc (30 mL) and H2O (10 mL). The organic layer was washed with brine (10 mL), dried (Na2SO4), and concentrated. The crude product was purified by flash chromatography using hexanes:ethyl acetate to give a pale yellow oil (615 mg, 65%): 1H NMR (400 MHz, CDCl3) δ 1.21 (t, 3H, J=7.3 Hz), 1.39 (s, 3H), 1.43 (s, 3H), 4.19 (q, 2H, J=7.3 Hz), 4.97 (s 2H), 6.00 (s, 1H), 6.61 (d, 1H, J=8.8 Hz), 6.74 (dd, 2H, J=3.2, 9.0 Hz), 6.96 (d, 1H, J=2.9 Hz), 7.22-7.39 (m, 10).

1. temperaturethe reaction mixture was heated for 40 h
2. temperatureThe mixture was cooled
3. custompartitioned between EtOAc (30 mL) and H2O (10 mL)
4. washThe organic layer was washed with brine (10 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customThe crude product was purified by flash chromatography

ORD record

ord-9bac0384fe264d7a85e124526aedbbe4

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982278B2