[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[I-].[K+].Cl[CH2:42][C:43](=[O:45])[CH3:44]>C(#N)C>[CH3:1][O:2][C:3](=[O:14])[CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])[CH2:42][C:43](=[O:45])[CH3:44]A three-neck round bottom flask with magnetic stirrer was charged with crude (2-nitro-phenyl)-acetic acid methyl ester (7.23 g, 37.0 mmol), potassium carbonate (46.1 g, 33.3 mmol), 18-crown-6 (0.650 g), and potassium iodide (0.650 g) under an argon atmosphere. To the flask was added acetonitrile (80 mL) and the mixture heated at 70° C. for one hour. To the reaction was added chloroacetone (3.50 mL, 44.0 mmol) and the reaction stirred at 70° C. under argon for 18-20 hours. The reaction was cooled to room temperature and filtered through a pad of celite. The resulting filtrate was concentrated in vacuo to afford 9.64 g of crude material. Purification via flash chromatography (0-40% ethyl acetate/hexanes eluent) yielded 4.74 g of 2-(2-nitro-phenyl)4-oxo-pentanoic acid methyl ester (51%).
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