Sodium Hydroxide → Ethyl 4-(4-bromophenyl)-4-oxo-2-(2-phenylethyl)butanoate

Temperature

50 °C

To a solution of diethyl 2-[2-(4-bromophenyl)-2-oxoethyl]-2-(2-phenylethyl)malonate (7.89 g, 17.1 mmol) in acetone (18.5 mL) and ethanol (17.0 mL) was added 1 N aqueous sodium hydroxide solution (17.1 mL), and the resulting solution was heated at 50° C. for 3 h. Solvent was then removed under reduced pressure via rotary evaporation and the resulting residue was further concentrated under high vacuum for 1 h. The residue was redissolved in dimethoxyethane (18.5 mL) and the solution was heated at 80° C. for 2.5 h. The mixture was cooled to rt, diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated under high vacuum. The resulting residue was purified by flash chromatography (Biotage flash 75, 10:90 ethyl acetate/hexane) to afford ethyl 4-(4-bromophenyl)-4-oxo-2-(2-phenylethyl)butanoate (4.32 g, 65%). LC-MS ret. time 3.79 min, m/z 389.2 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.20 (t, 3H), 1.78–1.94 (m, 2H), 2.62 (t, 2H), 2.86–3.01 (m, 2H), 3.26–3.36 (m, 1H), 4.10 (q, 2H), 7.05–7.11 (m, 3H), 7.18–7.23 (m, 2H), 7.51 (d, 2H), 7.72 (d, 2H).

1. customSolvent was then removed under reduced pressure via rotary evaporation
2. concentrationthe resulting residue was further concentrated under high vacuum for 1 h
3. dissolutionThe residue was redissolved in dimethoxyethane (18.5 mL)
4. temperaturethe solution was heated at 80° C. for 2.5 h
5. temperatureThe mixture was cooled to rt
6. additiondiluted with ethyl acetate
7. washwashed with water
8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
9. concentrationconcentrated under high vacuum
10. customThe resulting residue was purified by flash chromatography (Biotage flash 75, 10:90 ethyl acetate/hexane)

ORD record

ord-8fb6d4a6537a45d7bc04373d65cf36ce

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091228B2