[CH2:1]([CH:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=2[F:19])=[CH:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[H][H]>C1(C)C=CC=CC=1.[Pd]>[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=2[F:19])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]The compound (9) (50.0 g) was dissolved in a mixed solvent of toluene (150 ml) and Solmix A-11 (150 ml), Pd/C (0.5 g) was added thereto, and the mixture was stirred at room temperature under a hydrogen atmosphere until hydrogen absorption had ceased. After the reaction had been completed, Pd/C was removed and then the solvent was distilled off. The residue obtained was purified with a fractional operation by means of column chromatography using heptane as the eluent and silica gel as the stationary phase powder, and further purified by means of recrystallization from Solmix A-11 and dried, giving 47.0 g of 4-pentyl-(2,3-difluorophenyl)cyclohexane (10). The yield based on the compound (9) was 94.0%.
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