[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[CH:13]([OH:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]An anhydrous methylene chloride solution of 20.0 g of ethyl 3-(2,6-dichloro-4-trifluoromethylphenyl)-3-hydroxypropionate (8) was added to a suspension of 19.6 g of pyridinium chlorochromate and 15 g of Celite in 100 ml of methylene chloride at room temperature, and the mixture was stirred overnight. The reaction mixture was diluted with 200 ml of ether and thereafter applied to a column packed with 100 g of silica gel. Ether was used for elution, and the eluent was concentrated under reduced pressure, giving 8.3 g of the desired compound in the form of a pale brown oil (yield 41.91%).
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