Hydrochloric Acid → 3-(2,2-dimethyl4-oxo4H-1,3-benzodioxin-5-yl)-benzoic acid, ethyl ester

To a solution of 2,2-dimethyl-5-trifluoromethanesulfonyloxy-4H-1,3-benzodioxin-4-one (2.0 g, 5.8 mmol), 3-ethoxycarbonylphenylboronic acid (1.34 g, 6.9 mmol) and anhydrous K2CO3 powder (2.61 g, 18.9 mmol) in DMF (30 mL) was added tetrakis(triphenylphosphine)palladium (0.202 g, 0.175 mmol). The mixture was heated at reflux for 2 h. The reaction mixture was allowed to cool to room temperature (“rt”) and 1 N HCl (25 mL) was added. The mixture was extracted with EtOAc (3×25 mL). The combined extracts were washed with water and brine, then dried over MgSO4, filtered, and concentrated. The crude material was purified by flash chromatography (1:15 EtOAc/hexanes) to afford 3-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-5-yl)-benzoic acid, ethyl ester (1.2 g, 63%) as a white solid: 1H NMR (CDCl3) 1.39 (t, J=7.1 Hz, 3H), 1.80 (s, 6H), 4.39 (q, J=7.0 Hz, 2H), 7.01 (d, J=8.0 Hz, 2H), 7.47-7.57 (m, 3H), 8.00 (t, J=1.5 Hz, 1H), 8.07 (dt, J=7.5, 1.5 Hz, 1H).

1. temperatureThe mixture was heated
2. temperatureat reflux for 2 h
3. additionwas added
4. extractionThe mixture was extracted with EtOAc (3×25 mL)
5. washThe combined extracts were washed with water and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude material was purified by flash chromatography (1:15 EtOAc/hexanes)

ORDレコード

ord-091e931a818147d292c1d563df35f708

出典データセット

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07220780B2