[C:1]([O:13][CH3:14])(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O-:11])=O.C(Cl)(=O)C(Cl)=O.[C:21]1([CH2:27][CH2:28][CH2:29][CH2:30]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Mg].C1(CCCCBr)C=CC=CC=1.[Mg].[Cl-].[NH4+]>C1(C)C=CC=CC=1.O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[O:11]=[C:9]([CH2:30][CH2:29][CH2:28][CH2:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:13][CH3:14])=[O:12]A commercially available reagent of monomethyl azelate (2.73 g, 13.5 mmol) was dissolved in toluene (21 mL), and N,N-dimethylformamide (0.00085 mL, 0.110 mmol) and oxalyl chloride (1.5 mL, 11.8 mmol) were then added. The reaction mixture was stirred at 60° C. for 2 hours, and then concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (27 mL), and the solution was then cooled to −40° C. Iron (III) tris(acetylacetonate) (200 mg, 0.566 mmol) was added. Magnesium 4-phenylbutyl bromide, prepared beforehand, was then added dropwise over 10 minutes [Magnesium 4-phenylbutyl bromide was prepared as follows: 4-phenylbutyl bromide (2.96 g, 13.9 mmol) was dissolved in tetrahydrofuran (11 mL), and magnesium (337 mg, 13.9 mmol) was then added, and subsequently dissolved by stirring the mixture for 30 minutes with occasional warming by a dryer]. After 1.5 hours, ethyl acetate (100 mL) and a saturated aqueous solution (100 mL) of ammonium chloride were added. The outer temperature was then cooled to room temperature. After separation, the organic layer was washed with a saturated aqueous solution (100 mL) of sodium chloride. The solvent was then distilled off under reduced pressure. The residue was purified on Biotage (silica gel, n-hexane/ethyl acetate) to obtain 1.81 g (5.68 mmol, 42% yield) of methyl 9-oxo-13-phenyl-tridecanoate.
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