[Cl:1][C:2]1[CH:3]=[C:4]([C:11](=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:5]=[C:6]([F:10])[C:7]=1[O:8][CH3:9].C=O.[C:20](=O)([O-])[O-].[K+].[K+]>CO>[CH2:13]([CH:12]1[CH2:20][C:3]2[C:4](=[CH:5][C:6]([F:10])=[C:7]([O:8][CH3:9])[C:2]=2[Cl:1])[C:11]1=[O:17])[CH2:14][CH2:15][CH3:16]A mixture of the crude 1-(3-chloro-5-fluoro-4-methoxyphenyl)-1-hexanone from step 1, methanol (8.7 mL), 37% aqueous formaldehyde (0.786 mL, 10.5 mmol), and potassium carbonate (1.2 g, 8.72 mmol) was stirred and heated in an oil bath at 50° C. for 7 hours. The mixture was evaporated under vacuum and the residue partitioned between EtOAc (100 mL) and water (100 mL) containing 2N HCl (10 mL). The organic phase was washed with brine (50 mL), dried over MgSO4, filtered, and evaporated under vacuum to an oil (1.86 g) consisting of predominantly 1-(3-chloro-5-fluoro-4-methoxyphenyl)-2-(methoxymethyl)-1-hexanone.
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