C(O)C.[F:4][C:5]1[C:13]([F:14])=[C:12]([F:15])[CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([C@H:16]1[CH2:21][CH2:20][C@H:19]([CH2:22][CH2:23][CH3:24])[CH2:18][CH2:17]1)[CH2:9]2.[H][H]>[C].[Pd].C(OCC)(=O)C>[F:4][C:5]1[C:13]([F:14])=[C:12]([F:15])[CH:11]=[C:10]2[C:6]=1[CH2:7][CH:8]([C@H:16]1[CH2:21][CH2:20][C@H:19]([CH2:22][CH2:23][CH3:24])[CH2:18][CH2:17]1)[CH2:9]2Ethanol (70 ml), ethyl acetate (30 ml) and 5% palladium-carbon (450 mg) were added to 4,5,6-trifluoro-2-(trans-4-propylcyclohexyl)indene (4.5 g), and stirred for 1 hour in a hydrogen atmosphere. The reaction solution was filtered with celite, the filtrate was concentrated, and the residue was purified with a silica gel short column (hexane) to obtain 4,5,6-trifluoro-2-(trans-4-propylcyclohexyl)indane (4.5 g). Moreover, this was then recrystallized from ethanol to obtain 4,5,6-trifluoro-2-(trans-4-propylcyclohexyl)indane (4.5 g, purity: 99.8%). The melting point of this compound was 52° C.
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