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

HRID 2427302Notes

Reaction equation

HRID 2427302 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:29])[CH2:9][C:10]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(C(OCC)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.[OH-].[Na+]>CC(C)=O.C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:29])[CH2:9][CH:10]([CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21985802Diethyl 2-[2-(4-bromophenyl)-2-oxoethyl]-2-(2-phenylethyl)malonate

Product 1

HCID 21985805Ethyl 4-(4-bromophenyl)-4-oxo-2-(2-phenylethyl)butanoateYield 65%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-a35033bdaca74435819dd64ae88d2b79
Source dataset
uspto-grants-2011_06
Patent number
US07968576B2

Reaction notes

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