Ethanol → Ethyl 4-(3-methyl-4'-nitro-1,1'-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate

HRID 9561Notes

Reaction equation

HRID 9561 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=2)[CH:5]=[CH:6][C:7]=1[C:8](=[O:29])[CH2:9][C:10]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(C(OCC)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12].[OH-].[Na+].C(O)C>CC(C)=O>[CH3:1][C:2]1[CH:3]=[C:4]([C:30]2[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=2)[CH:5]=[CH:6][C:7]=1[C:8](=[O:29])[CH2:9][CH:10]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 21985780Diethyl 2-[2-(3-methyl-4'-nitro-1,1'-biphenyl-4-yl)-2-oxoethyl]-2-(2-phenylethyl)malonate

Product 1

HCID 21985781Ethyl 4-(3-methyl-4'-nitro-1,1'-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoateYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of diethyl 2-[2-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)-2-oxoethyl]-2-(2-phenylethyl)malonate (4.87 g, 9.41 mmol), 1 N aqueous sodium hydroxide (10.4 mL, 10.40 mmol), ethanol (10 mL), and acetone (10 mL) was stirred at 50° C. overnight. The mixture was concentrated and the residue was dissolved in dimethoxyethane (20 mL), and stirred at 80° C. overnight. The mixture was concentrated, and the residue was dissolved in ethyl acetate (30 mL). The solution was washed with water (2×5 mL), dried over magnesium sulfate, and concentrated under reduced pressure. The material obtained was purified by flash chromatography (10:90 ethyl acetate/hexane) to give ethyl 4-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate as a light yellow oil (3.53 g, 99% yield). LC-MS ret. time 4.18 min, m/z 446.0 (MH+); 1H NMR (CDCl3) δ: 1.33 (t, 3H), 1.83–2.17 (m, 2H), 2.58 (s, 3H), 2.67–2.78 (m, 2H), 3.00 (dd, 1H), 3.14 (m, 1H), 3.49 (dd, 1H), 4.09 (q, 2H), 7.14–7.36 (m, 5H), 7.47–7.55 (m, 2H), 7.72–7.83 (m, 3H), 8.33 (d, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in dimethoxyethane (20 mL)
  3. stirringstirred at 80° C. overnight
  4. concentrationThe mixture was concentrated
  5. dissolutionthe residue was dissolved in ethyl acetate (30 mL)
  6. washThe solution was washed with water (2×5 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe material obtained
  10. customwas purified by flash chromatography (10:90 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-dc5c41d608fa4163b1a900774a6d08b6
Source dataset
uspto-grants-2006_08
Patent number
US07091228B2

Reaction notes

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