Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][CH2:11][O:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1.C([Li])CCC.[Cl-].[Ce+3].[Cl-].[Cl-].[F:28][C:29]([F:34])([F:33])[C:30](=[O:32])[CH3:31]>O1CCCC1>[F:28][C:29]([F:34])([F:33])[C:30]([C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][CH2:11][O:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)([OH:32])[CH3:31]To a stirred solution of 2-(2-(2-bromo-5-methoxyphenyl)-ethoxy)tetrahydropyran (1.0 g, 3.17 mmol) in dry tetrahydrofuran (20 ml) was added n-butyllithium (2.5 ml, 4.12 mmol) dropwise under nitrogen at −78° C. The reaction mixture was stirred at −40° C. for 1 hr. To the reaction mixture was added a suspension of anhydrous cerium chloride (884 mg, 3.58 mmol) in dry tetrahydrofuran (15 ml) dropwise at −78° C. and stirred for 1 hr. To the reaction mixture was added trifluoroacetone (0.5 ml, 5.59 mmol), and the resulting mixture was stirred at −78° C. for 1 hr. This was quenched by saturated ammonium chloride solution, extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate, and concentrated to give a crude products, which were purified by silica-gel column chromatography eluted with a gradient of hexane and ethyl acetate (20:1, 15:1, 12:1, 10:1) to give the title compound (555 mg, 50.3%). 1H-NMR(CDCl3): 7.35-7.31 (m, 1H), 6.78-6.74 (m, 2H), 5.70 and 5.62 (each s, total 1H), 4.63 and 4.48 (each m, total 1H), 4.18-4.11 and 3.99-3.92 (each m, total 1H), 3.80 (s, 3H), 3.77-3.43 (m, 3H), 3.33-2.90 (m, 2H), 1.80 and 1.78 (each s, total 3H), 1.75-1.26 (m, 6H).
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