[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:10]([CH:13]1C(=O)OC(C)(C)[O:15][C:14]1=[O:22])[CH2:11][CH3:12].CN(C=O)C.O>CCOCC>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:10]([CH2:11][CH3:12])[CH2:13][C:14]([OH:22])=[O:15]A 500 mL round bottom flask was charged with 5-(1-(2-fluoro-3-methoxyphenyl)propyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 77.C (5.17 g, 16.7 mmol) and 10:1 DMF/water (80 mL). The pale yellow solution was stirred overnight at 90° C., cooled to room temperature, and diluted with ether. The combined organic layers were washed with water and brine, dried (MgSO4), and concentrated to afford 3-(2-fluoro-3-methoxyphenyl)pentanoic acid 77.D (3.44 g, 91.3% yield) as a yellow oil. The crude product was used without further purification.
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